Ruimao Hua

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Name: 华瑞茂; Hua, RuiMao

Organization: Tsinghua University , China

Department: Department of Chemistry

Title: Professor(PhD)

TOPICS

Polymer

UV Absorbents

Chemicals
References

Silver-catalyzed chemoselective annulation of propargyl amines with alkynes for access to pyridines and pyrroles

Co-reporter:Tauqir A. Nizami, Ruimao Hua

Tetrahedron 2017 Volume 73, Issue 42(Issue 42) pp:

Publication Date(Web):19 October 2017

DOI:10.1016/j.tet.2017.09.002

The annulation of propargyl amines with electron-deficient alkynes in the presence of silver salts affording pyridines and pyrroles has been developed. The chemoselective [4+2] or [3+2] annulation approach to pyridines or pyrroles depends on the structures of propargyl amines and the different reaction conditions.Download high-res image (148KB)Download full-size image

[Cu(maloNHC)]-catalyzed synthesis of 2-aryl pyrazolo[5,1-a]isoquinolines by annulation of N′-(2-((trimethylsilyl)ethynyl)benzylidene)hydrazides with terminal aromatic alkynes

Co-reporter:Huixin Liu, Le Lu, Ruimao Hua

Tetrahedron 2017 Volume 73, Issue 45(Issue 45) pp:

Publication Date(Web):9 November 2017

DOI:10.1016/j.tet.2017.09.037

A [Cu(maloNHC)]-catalyzed synthesis of 2-aryl pyrazolo[5,1-a]isoquinolines via annulation of N′-(2-((trimethylsilyl)ethynyl)benzylidene)hydrazides with terminal aromatic alkynes was developed.Download high-res image (191KB)Download full-size image

Synthesis of fused polycyclic indoles via Cu(II)-catalyzed intramolecular cyclization of N-(2-cyanophenyl)indoles in the presence of diaryliodonium salts

Co-reporter:Lei Zhang, Yunpeng Wang, Liyao Zheng, Biao Guo, Ruimao Hua

Tetrahedron 2017 Volume 73(Issue 4) pp:395-402

Publication Date(Web):26 January 2017

DOI:10.1016/j.tet.2016.12.022

A novel and mild method for the synthesis of fused polycyclic indoles of [1,2-a]indol-10-imines via a Cu(OTf)2-catalyzed the intramolecular cyclization of N-(2-cyanophenyl)indoles in the presence of diaryliodonium salts has been developed.

Base-promoted synthesis of 1H,3H-pyrrolo[1,2-c]thiazol-3-imine derivatives via [3+2] annulation of 2-alkynylpyrroles with isothiocyanates

Co-reporter:Ziyin Zhang, Biao Guo, Yiming Zhou, Ruimao Hua

Tetrahedron 2016 Volume 72(Issue 47) pp:7613-7619

Publication Date(Web):24 November 2016

DOI:10.1016/j.tet.2016.10.017

Base-promoted [3+2] annulation of 2-alkynyl pyrrole with isothiocyanate affording 1H,3H-pyrrolo[1,2-c]thiazol-3-imine derivatives has been developed. The control experiments suggest that the reaction proceeds via simple nucleophilic attack followed by intramolecular addition. The present cascade reaction provides a facile one-pot synthesis of 1H,3H-pyrrolo[1,2-c]thiazol-3-imine derivatives under mild conditions with good yields and high regioselectivity.

CuSO4·5H2O-catalyzed aminobenzannulation of ortho-alkynylaromatic ketones with anilines approach towards 1-aminonaphthalenes

Co-reporter:Biao Guo, Ruimao Hua

Tetrahedron 2016 Volume 72(Issue 30) pp:4608-4615

Publication Date(Web):28 July 2016

DOI:10.1016/j.tet.2016.06.036

An efficient catalyst system for the aminobenzannulation of ortho-alkynylaromatic ketones with amines affording substituted 1-aminonaphthalene derivatives with high atom-efficiency in the presence of CuSO4·5H2O was developed.

Conversion of carbon dioxide into 2-oxazolidinones and 2(3H)-oxazolones catalyzed by 2,2′,2″-terpyridine

Co-reporter:Huixin Liu, Ruimao Hua

Tetrahedron 2016 Volume 72(Issue 9) pp:1200-1204

Publication Date(Web):3 March 2016

DOI:10.1016/j.tet.2016.01.015

The catalytic activation of pyridines as organocatalysts in the three-component cycloaddition of CO2, propargyl alcohol and primary amine was investigated, and 2,2′,2″-Terpyridine was found to be the efficient organocatalyst to afford 4-methylene-2-oxazolidinones or 2(3H)-oxazolones in good to high yields. 2,2′,2″-Terpyridine also showed high catalytic activity in the coupling reaction of CO2 with aziridines bearing either electron-donating or electron-withdrawing N-substituents to give substituted 2-oxazolidinones in high yields.

Synthesis of Natural Product-like Polyheterocycles via One-Pot Cascade Oximation, C–H Activation, and Alkyne Annulation

Co-reporter:Liyao Zheng, Yunhui Bin, Yunpeng Wang, and Ruimao Hua

The Journal of Organic Chemistry 2016 Volume 81(Issue 19) pp:8911-8919

Publication Date(Web):September 14, 2016

DOI:10.1021/acs.joc.6b01460

An efficient protocol for the direct transformation of chroman-4-ones to tricyclic fused pyridines with the skeleton of cassiarins, a family of alkaloids with antimalarial activity, was developed. Also, a general strategy for modular construction of polyheterocycles with diverse natural product-like skeletons was developed by using ketone–alkyne bifunctional substrates. These reactions involved a one-pot cascade oximation of ketones, rhodium-catalyzed C–H activation, and intermolecular/intramolecular alkyne annulations under mild conditions with high atom, step, and redox economy.

Synthesis of Benzofulvene Derivatives from Diarylacetylenes via Pd(II)-Catalyzed Alkyne-Directed C(sp2)–H Bond Activation

Co-reporter:Biao Guo, Liyao Zheng, Lei Zhang, and Ruimao Hua

The Journal of Organic Chemistry 2015 Volume 80(Issue 16) pp:8430-8434

Publication Date(Web):August 4, 2015

DOI:10.1021/acs.joc.5b01304

A novel and efficient protocol for the synthesis of benzofulvene derivatives from easily available diarylacetylenes has been developed. The reaction proceeds through rarely reported carboxylate-assisted alkyne-directed ortho-C(sp2)–H palladation followed by insertion of another diarylacetylene.

Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ

Co-reporter:Biao Guo, Yiming Zhou, Lei Zhang, and Ruimao Hua

The Journal of Organic Chemistry 2015 Volume 80(Issue 15) pp:7635-7641

Publication Date(Web):July 16, 2015

DOI:10.1021/acs.joc.5b01219

Trifluoromethanesulfonic acid (HOTf) promoted cross-coupling of ortho-[2-(4-methoxylphenyl)-alkynyl]acetophenones with ortho-alkynylbenzaldehydes affording chrysene derivatives has been developed. The present cascade reaction provides a facile one-pot synthesis of multisubstituted chrysenes as well as naked chrysene under mild conditions. The mechanism experimental results demonstrate isochromenylium is a key intermediate for this transformation.

Multikilogram Scale Organolithiation Chemistry for the Manufacture of Liquid Crystal Intermediates

Co-reporter:Yao-Hua Han, Ting Zhou, Yan Sui, and Ruimao Hua

Organic Process Research & Development 2014 Volume 18(Issue 10) pp:1229-1233

Publication Date(Web):August 29, 2014

DOI:10.1021/op500133p

This paper describes the kilogram-scale regioselective synthesis of various fluorinated arylboronic acids, aryl iodides, aryl acids, aryl aldehydes, and cyclohexenyl-substituted aryls in good to high yields via in situ fluorine-directed ortho-lithiation of fluorinated aryls and their subsequent reactions in a one-pot manner with nucleophiles such as triisobutyl borate, iodine, carbon dioxide, N,N-dimethylformamide, and cyclohexyl ketones.

Synthesis and antiproliferative activity of RITA and its analogs

Co-reporter:Jianhua Jiang, Chao Ding, Lulu Li, Chunmei Gao, Yuyang Jiang, Chunyan Tan, Ruimao Hua

Tetrahedron Letters 2014 Volume 55(Issue 49) pp:6635-6638

Publication Date(Web):3 December 2014

DOI:10.1016/j.tetlet.2014.10.074

The synthesis of RITA and a variety of five-membered heterocyclic triads by the cyclocondensation of 1,4-bis(5-substituted-2-thienyl or 2-furyl)-1,3-butadiynes with water or Na2S·9H2O in the presence of KOH in DMSO is described. The study on the antiproliferative activities against K562, MCF-7, A549, and HCT116 tumor cells has revealed that some of the heterocyclic triads show higher antiproliferative activities than RITA, depending on the structures of substituents, the property of heteroatoms as well as their numbers.

Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and their behavior of liquid crystallines

Co-reporter:Jian Guo, Ruimao Hua, Yan Sui, Jianhua Cao

Tetrahedron Letters 2014 Volume 55(Issue 9) pp:1557-1560

Publication Date(Web):26 February 2014

DOI:10.1016/j.tetlet.2014.01.066

The synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by the cyclocondensation of amidoximes with trifluoroacetic anhydride or benzoic acid derivatives in moderate to high yields is described. The study on the phase transition behavior has disclosed that some of the synthesized oxadiazoles show smectic or nematic phases depending on their structures, which have the high potential application as liquid crystalline monomers.

Palladium-catalyzed direct intramolecular double α-C–H arylation of 1,5-diketone: a strategy for synthesis of Tröger’s base analogues

Co-reporter:Jia Ju, Lei Zhang, Ruimao Hua

Tetrahedron Letters 2014 Volume 55(Issue 22) pp:3374-3376

Publication Date(Web):28 May 2014

DOI:10.1016/j.tetlet.2014.04.069

9-Aryl-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-diones were straightforwardly prepared via a tandem reaction of easily available ortho-chloroacetophenone and ortho-chlorochalcone catalyzed by PdCl2(PCy3)2.

Modular Assembly of Ring-Fused and π-Extended Phenanthroimidazoles via C–H Activation and Alkyne Annulation

Co-reporter:Liyao Zheng and Ruimao Hua

The Journal of Organic Chemistry 2014 Volume 79(Issue 9) pp:3930-3936

Publication Date(Web):April 8, 2014

DOI:10.1021/jo500401n

π-Extension of 2-aryl-phenanthroimidazoles via rhodium(III)-catalyzed C–H activation and alkyne annulation is developed. This method enables rapid, practical and modular assembly of diverse ring-fused phenanthroimidazoles, including an unusual rearrangement product using aryl-alkyl asymmetric alkyne and a thiophene fused product which could serve as a Fe3+ fluorescent probe. The feasibility of the one-pot synthesis and ruthenium(II)-catalyzed versions of this reaction was also verified.

Synthesis of Chrysene Derivatives via Copper-Catalyzed One-Pot Dimerization of 2-Alkynyl-1-acetylbenzenes

Co-reporter:Biao Guo, Liyao Zheng, Lichen Yang, and Ruimao Hua

The Journal of Organic Chemistry 2014 Volume 79(Issue 10) pp:4352-4357

Publication Date(Web):April 18, 2014

DOI:10.1021/jo500182k

An efficient route for highly substituted chrysene derivatives via operationally simple copper-catalyzed one-pot dimerization of 2-alkynyl-1-acetylbenzenes is described.

Rhodium(III)-Catalyzed CH Activation and Indole Synthesis With Hydrazone as an Auto-Formed and Auto-Cleavable Directing Group

Co-reporter:Liyao Zheng ;Dr. Ruimao Hua

Chemistry - A European Journal 2014 Volume 20( Issue 8) pp:2352-2356

Publication Date(Web):

DOI:10.1002/chem.201304302

Abstract

An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for Rh^III-catalyzed CH activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and CO source, whereas its NN bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DG^auto). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DG^auto strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated.

One-Pot Synthesis of Multisubstituted 2-Aminoquinolines from Annulation of 1-Aryl Tetrazoles with Internal Alkynes via Double C–H Activation and Denitrogenation

Co-reporter:Lei Zhang, Liyao Zheng, Biao Guo, and Ruimao Hua

The Journal of Organic Chemistry 2014 Volume 79(Issue 23) pp:11541-11548

Publication Date(Web):November 12, 2014

DOI:10.1021/jo502192b

An efficient, one-pot synthesis of multisubstituted 2-aminoquinolines from 1-aryl tetrazoles and internal alkynes has been developed. The reaction involves cyclization of 1-aryl tetrazoles with internal alkynes via rhodium(III)-catalyzed double C–H activation and copper(II)-mediated denitrogenation.

A general approach to arylated furans, pyrroles, and thiophenes

Co-reporter:Qingwei Zheng, Ruimao Hua, Jianhua Jiang, Lei Zhang

Tetrahedron 2014 70(44) pp: 8252-8256

Publication Date(Web):

DOI:10.1016/j.tet.2014.09.025

Synthesis of 3-methyleneisoindolin-1-ones via palladium-catalyzed C–Cl bond cleavage and cyclocarbonylation of ortho-chloro ketimines

Co-reporter:Jia Ju, Chuanmei Qi, Liyao Zheng, Ruimao Hua

Tetrahedron Letters 2013 Volume 54(Issue 38) pp:5159-5161

Publication Date(Web):18 September 2013

DOI:10.1016/j.tetlet.2013.07.017

PdCl2(PCy3)2-catalyzed cyclocarbonylative coupling of ortho-chloro arylketimines with CO has been investigated to develop an efficient method for the synthesis of isoindolin-1-ones. The developed synthetic method has the advantages of having easily available starting materials, high atom-economy, and high selectivity.

Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes

Co-reporter:Liyao Zheng, Jia Ju, Yunhui Bin, and Ruimao Hua

The Journal of Organic Chemistry 2012 Volume 77(Issue 13) pp:5794-5800

Publication Date(Web):June 18, 2012

DOI:10.1021/jo3010414

An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.

Copper-catalyzed three-component one-pot synthesis of quinazolines

Co-reporter:Jia Ju, Ruimao Hua, Ji Su

Tetrahedron 2012 68(46) pp: 9364-9370

Publication Date(Web):

DOI:10.1016/j.tet.2012.09.035

ReCl(CO)5-catalyzed cyclocondensation of phenols with 2-methyl-3-butyn-2-ol to afford 2,2-dimethyl-2H-chromenes

Co-reporter:Hanxiang Zeng, Jia Ju, Ruimao Hua

Tetrahedron Letters 2011 Volume 52(Issue 30) pp:3926-3928

Publication Date(Web):27 July 2011

DOI:10.1016/j.tetlet.2011.05.093

A direct one-pot route for the synthesis of 2,2-dimethyl-2H-chromenes by Re(CO)5Cl-catalyzed cyclocondensation of phenols with 2-methyl-3-butyn-2-ol has been developed. The easy availability of starting materials, mild reaction conditions, high atom-efficiency, and the use of a recoverable catalyst are advantages of this procedure.

Copper(I)-catalyzed reaction of diaryl buta-1,3-diynes with cyclic amines: an atom-economic approach to amino-substituted naphthalene derivatives

Co-reporter:Hongbin Sun, Xiaoli Wu, Ruimao Hua

Tetrahedron Letters 2011 Volume 52(Issue 34) pp:4408-4411

Publication Date(Web):24 August 2011

DOI:10.1016/j.tetlet.2011.06.046

1,4-Diaryl-1,3-butadiynes react with cyclic amines, such as pyrrolidine, piperidine, and morpholine in the presence of a catalytic amount of CuCl to afford amino-substituted naphthalene derivatives with good to high yields. The new catalytic procedure provides an atom-economic, one-pot synthetic method for the synthesis of naphthalene derivatives from easily available 1,4-diaryl-1,3-butadiynes.

Stereodivergent Ruthenium-Catalyzed Transfer Semihydrogenation of Diaryl Alkynes

Co-reporter:Jie Li ; Ruimao Hua

Chemistry - A European Journal 2011 Volume 17( Issue 30) pp:8462-8465

Publication Date(Web):

DOI:10.1002/chem.201003662

Abstract

[Ru₃(CO)₁₂]-catalyzed transfer semihydrogenation of various functionalized diaryl alkynes with N,N-dimethylformamide (DMF) and water as hydrogen source affords cis- and trans-stilbenes. The stereodivergent approach can be switched by the use of acetic (HOAc) or trifluoroacetic (TFA) acid as additives. The catalytic processes can be applied to the synthesis of analogues of natural products such as cis-combretastatin A-4 and trans-resveratrol.

An alternative CuClpiperidine-catalyzed oxidative homocoupling of terminal alkynes affording 1,3-diynes in air

Co-reporter:Qingwei Zheng;Youzhi Wan

Applied Organometallic Chemistry 2010 Volume 24( Issue 4) pp:314-316

Publication Date(Web):

DOI:10.1002/aoc.1604

Abstract

CuCl with the use of a catalytic amount of piperidine as additive shows high catalytic activity for the oxidative homocoupling reactions of terminal alkynes in toluene at 60 °C in air to afford 1,3-diynes in high yields. Copyright © 2009 John Wiley & Sons, Ltd.

An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans

Co-reporter:Hongyong Shang;Qingwei Zheng;Jianli Zhang;Xiao Liang;Qiming Zhu

Applied Organometallic Chemistry 2010 Volume 24( Issue 6) pp:473-476

Publication Date(Web):

DOI:10.1002/aoc.1642

Abstract

An improved practical synthesis of liquid crystals of trans-cyclohexyltolans by Sonogashira cross-coupling reaction of 1-iodo-4-(trans-4-alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C (palladium on activated carbon) as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone–water (5:2 in volume) is described. The liquid crystals could be obtained in high yields as a solid with excellent purity by simple filtration, and the filtrate could be reused several times while still retaining high catalytic activity. Copyright © 2010 John Wiley & Sons, Ltd.

CuCl-catalyzed cycloaddition of 1,3-butadiynes with primary amines: an atom-economic process for synthesis of 1,2,5-trisubsituted pyrroles

Co-reporter:Qingwei Zheng, Ruimao Hua

Tetrahedron Letters 2010 Volume 51(Issue 34) pp:4512-4514

Publication Date(Web):25 August 2010

DOI:10.1016/j.tetlet.2010.06.092

1,3-Butadiynes underwent inter- and intramolecular double hydroamination with primary amines in the presence of CuCl at 100 °C to afford 1,2,5-trisubsituted pyrroles in good to high yields.

Palladium-catalyzed [3+2+1] cyclocarbonylative coupling of 1,3-cyclohexanediones, alkynes, and carbon monoxide: an atom-economic route to chromene-2,5-dione derivatives

Co-reporter:Bei Wu, Ruimao Hua

Tetrahedron Letters 2010 Volume 51(Issue 49) pp:6433-6435

Publication Date(Web):8 December 2010

DOI:10.1016/j.tetlet.2010.09.132

3,4,7,8-Tetrahydro-2H-chromene-2,5(6H)-dione derivatives were efficiently synthesized with excellent selectivity via a [3+2+1] cyclocarbonylative coupling of 1,3-cyclohexanediones, terminal alkynes, and CO catalyzed by Pd(PPh3)4.

Gold(I)-catalyzed direct C–H arylation of pyrazine and pyridine with aryl bromides

Co-reporter:Ming Li, Ruimao Hua

Tetrahedron Letters 2009 50(13) pp: 1478-1481

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.01.059

A domino three-component condensation of ortho-haloacetophenones with urea or amines: a novel one-pot synthesis of halogen-substituted quinolines

Co-reporter:Chuanmei Qi, Qingwei Zheng, Ruimao Hua

Tetrahedron 2009 65(7) pp: 1316-1320

Publication Date(Web):

DOI:10.1016/j.tet.2008.12.039

Rhodium(I)-Catalyzed Reductive Cyclocarbonylation of Internal Alkynes: Atom-Economic Process for Synthesis of 2-Cyclopenten-1-ones, 5-Alkylidenefuran-2(5H)-ones and Indan-1-ones

Co-reporter:Qiufeng Huang Dr. Dr.

Chemistry - A European Journal 2009 Volume 15( Issue 15) pp:3817-3822

Publication Date(Web):

DOI:10.1002/chem.200802462

Palladium-catalyzed Heck coupling of 2-vinylpyridine with aryl chlorides

Co-reporter:Ming Li

Applied Organometallic Chemistry 2008 Volume 22( Issue 7) pp:397-401

Publication Date(Web):

DOI:10.1002/aoc.1414

Abstract

An efficient PdCl₂(PCy₃)₂-catalyzed cross-coupling reaction of 2-vinylpyridine with aryl chlorides to afford trans-2-styrylpyridines with a variety of functional groups on the benzene ring is described. Copyright © 2008 John Wiley & Sons, Ltd.

Palladium-Catalyzed Efficient and One-Pot Synthesis of Diarylacetylenes from the Reaction of Aryl Chlorides with 2-Methyl-3-butyn-2-ol

Co-reporter:Chenyi Yi;Hanxiang Zeng;Qiufeng Huang

Advanced Synthesis & Catalysis 2007 Volume 349(Issue 10) pp:

Publication Date(Web):17 JUL 2007

DOI:10.1002/adsc.200600498

An efficient and practical synthetic method has been developed for the preparation of symmetrical diarylacetylenes from the direct reaction of aryl chlorides with 2-methyl-3-butyn-2-ol catalyzed by palladium(II) chloride-bis(tricyclohexylphosphine) [PdCl₂(PCy₃)₂] under mild reaction conditions. Unsymmetrical diarylated acetylenes could be also obtained by using two different aryl chlorides simultaneously. The catalytic procedure includes a novel one-pot palladium-catalyzed, double Sonogashira coupling of inactivated aryl chlorides without use of copper(I) as co-catalyst.

An Efficient Rhodium-Catalyzed Double Hydroaminocarbonylation of Alkynes with Carbon Monoxide and Amines Affording 1,4-Diamide Derivatives

Co-reporter:Qiufeng Huang

Advanced Synthesis & Catalysis 2007 Volume 349(Issue 6) pp:

Publication Date(Web):17 APR 2007

DOI:10.1002/adsc.200600466

The hydroaminocarbonylation of terminal alkynes with carbon monoxide and pyrrolidine or piperidine catalyzed by rhodium complexes affords 1,4-diamide derivatives in good to high yields.

A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1,2-disubstituted-3,4-dihydronaphthalenes catalysed by N,N-dimethylformamide dimethyl acetal

Co-reporter:Jia-Li Jiang, Jia Ju and Ruimao Hua

Organic & Biomolecular Chemistry 2007 vol. 5(Issue 12) pp:1854-1857

Publication Date(Web):17 May 2007

DOI:10.1039/B706768B

1,2-Disubstituted-3,4-dihydronaphthalenes could be conveniently synthesized with high yields by the cycloaddition reactions of easily available vinylarenes with electron-deficient alkynes such as dimethyl, or diethyl acetylenedicarboxylate, methyl phenylpropiolate in the presence of DMF·DMA (N,N-dimethylformamide dimethyl acetal) as organocatalyst.

ReCl(CO)5-catalyzed Reactions of Aromatic Compounds with 1,3,5-Trioxane or Aqueous Formaldehyde Affording Diarylmethanes

Co-reporter:Rui-Mao Hua;Jun-Yi He;Hong-Bin Sun

Chinese Journal of Chemistry 2007 Volume 25(Issue 1) pp:

Publication Date(Web):8 JAN 2007

DOI:10.1002/cjoc.200790009

ReCl(CO)₅ catalyzed the dehydration reaction of aromatic compounds with 1,3,5-trioxane or aqueous formaldehyde (37 wt%) under air. The reactions of a variety of aromatic compounds bearing electron-donating group(s) with 1,3,5-trioxane afforded the corresponding diarylmethanes in moderate to good yields.

Rhodium-Catalyzed [2+2+1+1] Cyclocarbonylative Coupling of Alkynes with Carbon Monoxide Affording Tetrasubstituted p-Benzoquinones

Co-reporter:Qiufeng Huang

Chemistry - A European Journal 2007 Volume 13(Issue 29) pp:

Publication Date(Web):19 JUL 2007

DOI:10.1002/chem.200700839

In this strategy, the tetrasubstituted benzoquinones have been prepared directly by a [2+2+1+1] cyclocarbonylative coupling reaction of internal alkynes with CO in the presence of [RhCl(CO)₂]₂. The low concentration of CO in the reaction is the crucial point for the chemoselective formation of tetrasubstituted benzoquinones in good to high yields. Functional groups such as chloro, methoxy, cyano, vinyl, fluoro, and carboxylate are tolerated under the reaction conditions.

An Efficient Bismuth(III) Chloride-Catalyzed Synthesis of 1,1-Diarylalkenes via Friedel–Crafts Reaction of Acyl Chloride or Vinyl Chloride with Arenes

Co-reporter:Hongbin Sun;Songjie Chen;Yingwu Yin

Advanced Synthesis & Catalysis 2006 Volume 348(Issue 14) pp:

Publication Date(Web):12 SEP 2006

DOI:10.1002/adsc.200606157

In the presence of catalytic amount of bismuth(III) chloride, the reactions of acyl chlorides or vinyl chlorides with arenes afforded 1,1-diarylalkenes in 25–82 % isolated yield. In the case of the reaction of acyl chlorides with arenes, the procedure includes an initial Friedel–Crafts acylation, subsequent formation of vinyl chlorides and final Friedel–Crafts-type vinylation of another arene molecule with vinyl chloride. This paper reports the first Lewis acid-catalyzed cleavage of the CCl bond of vinyl chloride and its application in the synthesis of multiply subtituted alkenes.

Highly Regioselective Rhenium-Catalyzed Hydrosilylation of Styrenes

Co-reporter:Wen-Guo Zhao

European Journal of Organic Chemistry 2006 Volume 2006(Issue 24) pp:

Publication Date(Web):19 OCT 2006

DOI:10.1002/ejoc.200600555

The addition reaction of silanes to styrenes is efficiently catalyzed by ReBr(CO)₅ in toluene heated at 120 °C and selectively affords anti-Markovnikov adducts in good to high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

An Efficient and Selective Hydroarylation of Styrenes with Electron-Rich Arenes, Catalyzed by Bismuth(III) Chloride and Affording Markovnikov Adducts

Co-reporter:Hong-Bin Sun;Biao Li;Yingwu Yin

European Journal of Organic Chemistry 2006 Volume 2006(Issue 18) pp:

Publication Date(Web):10 JUL 2006

DOI:10.1002/ejoc.200600390

In the presence of BiCl₃, the hydroarylation of styrenes with electron-rich arenes afforded Markovnikov adducts selectively in good to high yields. Under arene-free conditions, the intermolecular hydroarylation of α-substituted styrenes and subsequent intramolecular hydroarylation produced the cyclic dimers of α-substituted styrenes in good yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Heteropolyacid-catalyzed Reaction of Epoxides with Ketones: Efficient Synthesis of 1,3-Dioxolane Derivatives

Co-reporter:Jun-Yi He;Fei-Xue Gao;Rui-Mao Hua

Chinese Journal of Chemistry 2005 Volume 23(Issue 9) pp:

Publication Date(Web):12 OCT 2005

DOI:10.1002/cjoc.200591275

An efficient method for the preparation of 1,3-dioxolanes via the coupling of epoxides with ketones catalyzed by heteropolyacids at ambient temperature has been described.

Novel C–N bond cleavage and formation in the polyoxometalates-catalyzed oxidation of nitroaromatics with 30% aqueous H2O2: An unprecedented disproportionation of nitroaromatics affording dinitroaromatics

Co-reporter:Feixue Gao, Ruimao Hua

Inorganica Chimica Acta 2005 Volume 358(Issue 13) pp:4045-4048

Publication Date(Web):1 September 2005

DOI:10.1016/j.ica.2005.07.004

In the presence of catalytic amount of K7NiV13O38 · 16H2O and 30% aqueous hydrogen peroxide, the disproportionation of nitroaromatic compounds occurs to give dinitro-substituted aromatic compounds. This novel disproportionation has disclosed an unprecedented process in which the carbon–nitrogen bond is catalytically cleaved and formed.In the presence of catalytic amount of K7NiV13O38 · 16H2O and 30% aqueous hydrogen peroxide, the disproportionation of nitroaromatic compounds occurs to give dinitro-substituted aromatic compounds.

A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1,2-disubstituted-3,4-dihydronaphthalenes catalysed by N,N-dimethylformamide dimethyl acetal

Co-reporter:Jia-Li Jiang, Jia Ju and Ruimao Hua

Organic & Biomolecular Chemistry 2007 - vol. 5(Issue 12) pp:NaN1857-1857

Publication Date(Web):2007/05/17

DOI:10.1039/B706768B