Zhi-Zhen Huang

Name: 黄志真; Huang, ZhiZhen

Organization: Zhejiang University , China

Department: Department of Chemistry

Title: Professor(PhD)

Chemicals
References

A Cascade Dehydrogenative Cross-Coupling/Annulation Reaction of Benzamides with β-Keto Esters for the Synthesis of Isoquinolinone Derivatives

Co-reporter:Guo-Dong Xu and Zhi-Zhen Huang

Organic Letters December 1, 2017 Volume 19(Issue 23) pp:6265-6265

Publication Date(Web):November 20, 2017

DOI:10.1021/acs.orglett.7b02978

A novel cascade DCC/annulation reaction of N-alkoxybenzamides with β-keto esters has been developed for the synthesis of isoquinolinone derivatives under palladium catalysis. A plausible mechanism involving α-C(sp2)–H activation and a Pd(II)/Pd(IV) catalytic cycle is also proposed.

A cascade C–H functionalization/cyclization reaction of N-arylpyridin-2-amines with α,β-unsaturated aldehydes for the synthesis of dihydroquinolinone derivatives under rhodium catalysis

Co-reporter:Zi-Jun Wu;Kenneth L. Huang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 23) pp:4978-4983

Publication Date(Web):2017/06/14

DOI:10.1039/C7OB00743D

A novel cascade C–H functionalization/cyclization reaction of N-arylpyridin-2-amines with α,β-unsaturated aldehydes has been developed under rhodium catalysis, affording dihydroquinolinone derivatives in moderate to excellent yields. A plausible mechanism of dual catalytic cycles by rhodium(III) catalysis is also proposed.

Cascade C–H Functionalization/Amidation Reaction for Synthesis of Azepinone Derivatives

Co-reporter:Peng Bai, Xing-Fen Huang, Guo-Dong Xu, and Zhi-Zhen Huang

Organic Letters 2016 Volume 18(Issue 13) pp:3058-3061

Publication Date(Web):June 16, 2016

DOI:10.1021/acs.orglett.6b01140

A cascade C–H functionalization/amidation reaction of aminobiaryls with diazomalonates has been developed under rhodium catalysis, affording new azepinone derivatives in moderate to excellent yields.

Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters

Co-reporter:Muhammad Salman, Zhi-Qiang Zhu, and Zhi-Zhen Huang

Organic Letters 2016 Volume 18(Issue 7) pp:1526-1529

Publication Date(Web):March 17, 2016

DOI:10.1021/acs.orglett.6b00162

A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired α-aryl α -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed.

Morita–Baylis–Hillman Reaction of α,β-Unsaturated Ketones with Allylic Acetates by the Combination of Transition-Metal Catalysis and Organomediation

Co-reporter:Ya-Qiong Li, Hai-Jun Wang, and Zhi-Zhen Huang

The Journal of Organic Chemistry 2016 Volume 81(Issue 11) pp:4429-4433

Publication Date(Web):May 17, 2016

DOI:10.1021/acs.joc.6b00684

An intermolecular Morita–Baylis–Hillman (MBH) reaction of α,β-unsaturated ketones with allylic acetates under the catalysis of 10 mol % of tetrakis(triphenylphosphine)palladium(0) and mediation of tributylphosphine has been developed in the presence of acetic acid, affording the desired α-coupling products. The MBH reaction has the advantages of good tolerance to many functional groups, excellent regioselectivity and E-stereoselectivity, and moderate to good yields.

A dehydrogenative cross-coupling reaction between aromatic aldehydes or ketones and dialkyl H-phosphonates for formyl or acylphenylphosphonates

Co-reporter:Xing-Fen Huang, Qing-Lai Wu, Jian-Shi He and Zhi-Zhen Huang

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 15) pp:4466-4472

Publication Date(Web):16 Mar 2015

DOI:10.1039/C5OB00161G

A novel DCC reaction between aromatic aldehydes or ketones and H-phosphonates has been developed for the synthesis of p-formyl or p-acylphenylphosphonates. The synthetic method has excellent para regioselectivities, good yields, and broad substrate scopes and is more benign to the environment. The DCC reaction also tolerates many functional groups, and results in a series of new p-formyl and p-acylphenylphosphonates, which should be important building blocks for the synthesis of versatile arylphosphonate derivatives.

Domino Reactions Containing Different Types of Heck Reactions for Selective 3,3- and 1,3-Diarylations of Propenol with Aryl Halides by Triple Catalysis

Co-reporter:Zhi-Qiang Zhu, Jian-Shi He, Hai-Jun Wang, and Zhi-Zhen Huang

The Journal of Organic Chemistry 2015 Volume 80(Issue 18) pp:9354-9359

Publication Date(Web):September 3, 2015

DOI:10.1021/acs.joc.5b01650

A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis.

Dehydrogenative Cross-Coupling Reaction by Cooperative Transition-Metal and Brønsted Acid Catalysis for the Synthesis of β-Quinolinyl α-Amino Acid Esters

Co-reporter:Zhi-Qiang Zhu, Peng Bai, and Zhi-Zhen Huang

Organic Letters 2014 Volume 16(Issue 18) pp:4881-4883

Publication Date(Web):September 9, 2014

DOI:10.1021/ol502402s

A novel dehydrogenative cross-coupling (DCC) reaction between methylquinoline derivatives and N-aryl glycine esters was developed by a cooperative catalysis of copper salt and Brønsted acid, affording an efficient synthesis of β-quinolinyl α-amino acid esters. A plausible mechanism using a proton to activate the methylquinoline derivative and copper(II) to activate N-aryl glycine ester has been proposed.

A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp3)–H/C(sp2)–H functionalizations

Co-reporter:Zhi-Qiang Zhu, Tian-Tian Wang, Peng Bai and Zhi-Zhen Huang

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 31) pp:5839-5842

Publication Date(Web):04 Jul 2014

DOI:10.1039/C4OB01256A

A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines has been developed through dual C(sp3)–H/C(sp2)–H functionalizations. The synthetic method has the advantages of high yields, good compatibility of functional groups and mild reaction conditions, although very unreactive alkanes were involved in the reaction. A plausible mechanism through both copper-catalyzed and DTBP mediated pathways has also been proposed.

Direct N-alkylation of amines with alcohols using AlCl3 as a Lewis acid

Co-reporter:Ya-Qiong Li, Yun-Bin Chen, Zhi-Zhen Huang

Chinese Chemical Letters 2014 Volume 25(Issue 12) pp:1540-1544

Publication Date(Web):December 2014

DOI:10.1016/j.cclet.2014.07.006

A substitution reaction of amines with alcohols for N-alkylated amines has been developed using inexpensive AlCl3 without any ligand or additive. Either aromatic or aliphatic amines and primary or secondary alcohols perform the AlCl3-mediated reaction smoothly to afford various N-alkylated amines in satisfactory yields.A direct N-alkylation of amines with alcohols has been developed using AlCl3 as a Lewis acid. Either aromatic or aliphatic amines and primary or secondary alcohols perform the AlCl3-mediated reaction smoothly to afford various N-alkylated amines.

Direct Coupling Reaction of Diaryl Methanol with Ketones or Aldehydes Catalyzed by AlCl3

Co-reporter:Zhiqiang Zhu;Peng Bai;Tiantian Wang;Zhizhen Huang

Chinese Journal of Chemistry 2014 Volume 32( Issue 11) pp:1176-1182

Publication Date(Web):

DOI:10.1002/cjoc.201400516

Abstract

A novel coupling reaction of diaryl methanols with ketones or aldehydes has been developed under the catalysis of AlCl₃. Various ketones and aldehydes could couple with 9H-xanthen-9-ol smoothly, affording coupling products in 48% –88% yields. A plausible mechanism using AlCl₃ to activate both diaryl methanol and ketone or aldehyde is proposed.

Copper-Catalyzed Dehydrogenative Cross-Coupling Reaction between Allylic CH Bonds and -CH Bonds of Ketones or Aldehydes

Co-reporter:Xing-Fen Huang;Muhammad Salman; Zhi-Zhen Huang

Chemistry - A European Journal 2014 Volume 20( Issue 22) pp:6618-6621

Publication Date(Web):

DOI:10.1002/chem.201402114

Abstract

A dehydrogenative cross-coupling reaction between allylic CH bonds and the α-CH bond of ketones or aldehydes was developed using Cu(OTf)₂ as a catalyst and DDQ as an oxidant. This synthetic approach to γ,δ-unsaturated ketones and aldehydes has the advantages of broad scope for both ketones and aldehydes as reactants, mild reaction conditions, good yields and atom economy. A plausible mechanism using Cu(OTf)₂ as a Lewis acid catalyst was also proposed (DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone; Tf=trifluoromethanesulfonate).

Copper-catalyzed dehydrogenative cross-coupling reaction between unactivated ethers and simple ketones mediated by pyrrolidine

Co-reporter:Xing-Fen Huang, Zhi-Qiang Zhu, Zhi-Zhen Huang

Tetrahedron 2013 69(40) pp: 8579-8582

Publication Date(Web):

DOI:10.1016/j.tet.2013.07.085

A cascade C–H functionalization/cyclization reaction of N-arylpyridin-2-amines with α,β-unsaturated aldehydes for the synthesis of dihydroquinolinone derivatives under rhodium catalysis

Co-reporter:Zi-Jun Wu, Kenneth L. Huang and Zhi-Zhen Huang

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 23) pp:NaN4983-4983

Publication Date(Web):2017/05/31

DOI:10.1039/C7OB00743D

A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp3)–H/C(sp2)–H functionalizations

Co-reporter:Zhi-Qiang Zhu, Tian-Tian Wang, Peng Bai and Zhi-Zhen Huang