Chuan-ying Li

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Organization: Zhejiang Sci-Tech University

Department: Department of Chemistry

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TOPICS

Organic Chemistry

allene

Chemicals
References

Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

Co-reporter:Haican Dai;Sisi Yu;Wanli Cheng;Ze-Feng Xu

Chemical Communications 2017 vol. 53(Issue 48) pp:6417-6420

Publication Date(Web):2017/06/13

DOI:10.1039/C7CC02521A

A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.

Metal-free synthesis of 2-aminonaphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles

Co-reporter:Ze-Feng Xu;Xing Yu;Dongdong Yang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 15) pp:3161-3164

Publication Date(Web):2017/04/11

DOI:10.1039/C7OB00637C

A facile metal-free synthesis of naphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles was realized. The in situ formed ketenimine was proposed as the key intermediate, and the desired 2-aminonaphthalenes were generated in up to 87% yield in refluxing 1,2-dichloroethane without any catalyst or additive.

Synthesis of Multifunctionalized 2-Carbonylpyrrole by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with β-Diketone

Co-reporter:Wanli Cheng, Yanhua Tang, Ze-Feng Xu, and Chuan-Ying Li

Organic Letters 2016 Volume 18(Issue 23) pp:6168-6171

Publication Date(Web):November 16, 2016

DOI:10.1021/acs.orglett.6b03179

A facile rhodium-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with β-diketones was realized, and a series of multisubstituted 2-carbonylpyrroles were synthesized efficiently (up to 94% yield). The protocol features several advantages, such as readily available materials, mild reaction conditions, a concise operating procedure, a broad reaction scope, and excellent regioselectivity when benzoylacetone derivatives were used.

Synthesis of 5-Iodo-1,2,3,4-tetrahydropyridines by Rhodium-Catalyzed Tandem Nucleophilic Attacks Involving 1-Sulfonyl-1,2,3-triazoles and Iodides

Co-reporter:Zengming Man, Haican Dai, Yinping Shi, Dongdong Yang, and Chuan-Ying Li

Organic Letters 2016 Volume 18(Issue 19) pp:4962-4965

Publication Date(Web):September 28, 2016

DOI:10.1021/acs.orglett.6b02428

Sodium iodide is used for the first time as a nucleophile to trap an α-imino rhodium carbene, which triggers a tandem process involving intermolecular nucleophilic attack and intramolecular SN2 reaction. A series of 5-iodo-1,2,3,4-tetrahydropyridines are obtained in high yield, and the synthetic utility of the products is demonstrated in cross-coupling reactions and the construction of biorelated polycyclic compounds.

Rhodium-Catalyzed Synthesis of 4-Bromo-1,2-dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an -Imino Carbene

Co-reporter:Jun He;Yinping Shi;Wanli Cheng;Zengming Man;Dongdong Yang ;Dr. Chuan-Ying Li

Angewandte Chemie 2016 Volume 128( Issue 14) pp:4633-4637

Publication Date(Web):

DOI:10.1002/ange.201512015

Abstract

Highly functionalized 4-bromo-1,2-dihydroisoquinolines were synthesized from readily available 4-(2-(bromomethyl)phenyl)-1-sulfonyl-1,2,3-triazoles. A bromonium ylide is proposed as the key intermediate, which can be formed by the intramolecular nucleophilic attack of the benzyl bromide on the α-imino rhodium carbene formed in the presence of the rhodium catalyst.

Rhodium-Catalyzed Synthesis of 4-Bromo-1,2-dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an -Imino Carbene

Co-reporter:Jun He;Yinping Shi;Wanli Cheng;Zengming Man;Dongdong Yang ;Dr. Chuan-Ying Li

Angewandte Chemie International Edition 2016 Volume 55( Issue 14) pp:4557-4561

Publication Date(Web):

DOI:10.1002/anie.201512015

Abstract

Rhodium-Catalyzed Synthesis of 2,5-Epoxybenzo[f][1,4]oxazepines by Tandem Reaction of 1-Sulfonyl-1,2,3-triazoles and Salicylaldehydes

Co-reporter:Yinping Shi;Xing Yu

European Journal of Organic Chemistry 2015 Volume 2015( Issue 29) pp:6429-6433

Publication Date(Web):

DOI:10.1002/ejoc.201500912

Abstract

Readily available 1-sulfonyl-1,2,3-triazoles were converted into α-imino carbenes in the presence of catalytic amounts of rhodium(II) salts. The carbenes underwent a tandem reaction with salicylaldehydes to provide a series of functionalized 2,5-epoxybenzo[f][1,4]oxazepines in high yields.

Synthesis of β-Amino-α,β-unsaturated Ketone Derivatives via Sequential Rhodium-Catalyzed Sulfur Ylide Formation/Rearrangement

Co-reporter:Jun He, Zengming Man, Yinping Shi, and Chuan-Ying Li

The Journal of Organic Chemistry 2015 Volume 80(Issue 9) pp:4816-4823

Publication Date(Web):April 9, 2015

DOI:10.1021/acs.joc.5b00521

In the presence of a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.

Synthesis of 3-Pyrrolin-2-ones by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with Ketene Silyl Acetal

Co-reporter:Rui-Qiao Ran, Jun He, Shi-Dong Xiu, Kai-Bing Wang, and Chuan-Ying Li

Organic Letters 2014 Volume 16(Issue 14) pp:3704-3707

Publication Date(Web):July 8, 2014

DOI:10.1021/ol501514b

α-Imino rhodium carbenoids generated from 1-sulfonyl 1,2,3-triazole were applied to the 3 + 2 cycloaddition with ketene silyl acetal, offering a novel and straightforward synthesis of biologically interesting compound 3-pyrrolin-2-one with broad substrate scope.

Synthesis of N-Acylamidines via Rhodium-Catalyzed Reaction of Nitrosobenzene Derivatives with N-Sulfonyl-1,2,3-triazoles

Co-reporter:Rui-Qiao Ran, Shi-Dong Xiu, and Chuan-Ying Li

Organic Letters 2014 Volume 16(Issue 24) pp:6394-6396

Publication Date(Web):December 8, 2014

DOI:10.1021/ol5031876

α-Imino rhodium carbene, readily generated from N-sulfonyl-1,2,3-triazole, underwent cycloaddition and subsequent rearrangement with a nitrosobenzene derivative to afford N-acylamidine. The unprecedented C–C bond cleavage of α-imino carbene was facilitated by the weakness of the N–O bond.

Synthesis of 3-Aza-bicyclo[3.1.0]hexan-2-one Derivatives via Gold-Catalyzed Oxidative Cyclopropanation of N-Allylynamides

Co-reporter:Kai-Bing Wang, Rui-Qiao Ran, Shi-Dong Xiu, and Chuan-Ying Li

Organic Letters 2013 Volume 15(Issue 10) pp:2374-2377

Publication Date(Web):May 7, 2013

DOI:10.1021/ol4007629

N-Allylynamides with various functional groups and different substitution patterns can be converted into 3-aza-bicyclo[3.1.0]hexan-2-one derivatives in moderate to high yield using IMesAuCl/AgBF4 as the catalyst and pyridine N-oxide as the oxidant. A noncarbene mediated approach is proposed as the mechanism.

Synthesis of Oxindoles through the Gold-Catalyzed Oxidation of N-Arylynamides

Co-reporter:Liu-Qing Yang;Kai-Bing Wang

European Journal of Organic Chemistry 2013 Volume 2013( Issue 14) pp:2775-2779

Publication Date(Web):

DOI:10.1002/ejoc.201300162

Abstract

α-Oxo gold carbenoids generated by the oxidation of N-arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N-oxide works as the oxidant, ligand, and base in this transformation.

Gold-Catalyzed Oxidative Rearrangement of Homopropargylic Ether via Oxonium Ylide

Co-reporter:Mei Xu, Tian-Tian Ren, and Chuan-Ying Li

Organic Letters 2012 Volume 14(Issue 18) pp:4902-4905

Publication Date(Web):September 6, 2012

DOI:10.1021/ol302238t

Synthetically useful α,β-unsaturated carbonyl compounds were obtained from gold-catalyzed oxidative rearrangement of homopropargylic ether under mild reaction conditions. Gold carbenoid and oxonium ylide are proposed as key intermediates.

Synthesis of Allenes via Gold-Catalyzed Intermolecular Reaction of Propargylic Alcohols and Aromatic Compounds

Co-reporter:Cheng-Fu Xu, Mei Xu, Liu-Qing Yang, and Chuan-Ying Li

The Journal of Organic Chemistry 2012 Volume 77(Issue 6) pp:3010-3016

Publication Date(Web):February 22, 2012

DOI:10.1021/jo300147u

Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.

Rhodium-catalyzed synthesis of multi-substituted furans from N-sulfonyl-1,2,3-triazoles bearing a tethered carbonyl group

Co-reporter:Wen-Biao Zhang, Shi-Dong Xiu and Chuan-Ying Li

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 1) pp:NaN50-50

Publication Date(Web):2014/11/28

DOI:10.1039/C4QO00273C

The efficient synthesis of highly functionalized furan derivatives from 1-sulfonyl-1,2,3-triazoles with a pendent carbonyl group is reported. The process involves an intramolecular trapping of α-imino carbene and subsequent aromatization.

Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

Co-reporter:Haican Dai, Sisi Yu, Wanli Cheng, Ze-Feng Xu and Chuan-Ying Li

Chemical Communications 2017 - vol. 53(Issue 48) pp:NaN6420-6420

Publication Date(Web):2017/05/09

DOI:10.1039/C7CC02521A

Metal-free synthesis of 2-aminonaphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles

Co-reporter:Ze-Feng Xu, Xing Yu, Dongdong Yang and Chuan-Ying Li

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 15) pp:NaN3164-3164

Publication Date(Web):2017/03/20

DOI:10.1039/C7OB00637C