Lei Zhou

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Name: 周磊; Zhou, Lei

Organization: Sun Yat-Sen University , China

Department: School of Chemistry and Chemical Engineering

Title: (PhD)

Chemicals
References

Synthesis of 3-Aryl-2-pyrones by Palladium-Catalyzed Cross-Coupling of Aryl Iodides with Cyclic Vinyldiazo Ester

Co-reporter:Jun Huang, Linyong Li, Haoguo Chen, Tiebo Xiao, Yuwei He, and Lei Zhou

The Journal of Organic Chemistry September 1, 2017 Volume 82(Issue 17) pp:9204-9204

Publication Date(Web):August 8, 2017

DOI:10.1021/acs.joc.7b01470

A palladium-catalyzed cross-coupling reaction of aryl iodides with cyclic vinyldiazo ester was developed. The reaction provides various 3-aryl-2-pyrones in good yields with high functional group tolerance. The synthetic application of the resulting 3-aryl-2-pyrones as the diene component in a Diels–Alder reaction was also described.

Visible-light promoted γ-cyanoalkyl radical generation: three-component cyanopropylation/etherification of unactivated alkenes

Co-reporter:Linyong Li;Haoguo Chen;Mingjing Mei

Chemical Communications 2017 vol. 53(Issue 84) pp:11544-11547

Publication Date(Web):2017/10/19

DOI:10.1039/C7CC07347J

A photoredox approach to generate distal cyano-substituted alkyl radicals through C–C bond cleavage of cyclobutanone oximes was developed. The radicals produced by this method were applied to three-component cyanopropylation/etherification of unactivated alkenes. Their reactions with diverse radical acceptors were also demonstrated.

Visible-Light-Mediated Two-Fold Unsymmetrical C(sp3)−H Functionalization and Double C−F Substitution

Co-reporter:

Chemistry - A European Journal 2017 Volume 23(Issue 10) pp:2249-2254

Publication Date(Web):2017/02/16

DOI:10.1002/chem.201605919

AbstractA visible-light-mediated [3+3] annulation of tertiary amines with α-trifluoromethyl alkenes was developed. The reaction offers a direct route to fluorinated tetrahydropyridines and azabicyclo[3.m.1] frameworks under very mild conditions. This protocol presents a rare example of dual sp3 C−H functionalization of tertiary amines with the formation of two different C−C bonds (one sp3–sp3 bond, one sp2–sp3 bond). Moreover, two consecutive C−F substitutions in a trifluoromethyl group were achieved in one pot using visible light photoredox catalysis, which enables an unprecedented ring construction.

Silver-catalyzed geminal aminofluorination of diazoketones with anilines and N-fluorobenzenesulphonimide

Co-reporter:Jun Huang;Linyong Li;Haoguo Chen;Tiebo Xiao;Yuwei He

Organic Chemistry Frontiers 2017 vol. 4(Issue 4) pp:529-533

Publication Date(Web):2017/03/28

DOI:10.1039/C6QO00813E

A silver-catalyzed three-component reaction of diazoketones, anilines and NFSI is developed. The reaction provides a new method for gem-aminofluorination of acceptor diazo compounds with aniline as the nitrogen source and NFSI as the fluorine source.

Synthesis of Gem-Difluorinated Fused Quinolines via Visible Light-Mediated Cascade Radical Cyclization

Co-reporter:Tiebo Xiao, Linyong Li, Yang Xie, Zong-Wan Mao, and Lei Zhou

Organic Letters 2016 Volume 18(Issue 5) pp:1004-1007

Publication Date(Web):February 25, 2016

DOI:10.1021/acs.orglett.6b00119

A facile synthesis of gem-difluorinated fused quinolines via visible light-mediated cascade radical cyclization between functionalized difluoromethyl chlorides and alkenes was developed. Various highly functionalized fused quinolines were assembled in moderate to good yields under very mild reaction conditions. The reaction extends the applications of chlorodifluoroacetic acid as the gem-difluoromethylenated building block by simple derivatization, especially in the synthesis of gem-difluorinated fused heterocyclic rings, which are difficult to access with existing methods.

Synthesis of N-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis

Co-reporter:Lei Zhou;Mohammad Lokman Hossain;Tiebo Xiao

The Chemical Record 2016 Volume 16( Issue 1) pp:319-334

Publication Date(Web):

DOI:10.1002/tcr.201500228

Abstract

Nitrogen heterocycles represent a highly important class of compounds which are widely used in materials science, agrochemistry, and medicinal chemistry. Therefore, there is continuing interest in the development of convenient, efficient, and environmentally benign synthetic methods for the construction of nitrogen containing heterocycles. Due to its natural abundance, ease of use, and promising application in industry, the use of visible light as a driving force for chemical reactions has received considerable attention in the past few years. This account summarizes the synthesis of N-heterocycles using visible-light photoredox catalysis published in the last two years, according to the size and type of the formed N-heterocyclic rings. In the context of seminal works of others in this area, a concise summary of the contributions of the authors is also offered.

Synthesis of Functionalized gem-Difluoroalkenes via a Photocatalytic Decarboxylative/Defluorinative Reaction

Co-reporter:Tiebo Xiao, Linyong Li, and Lei Zhou

The Journal of Organic Chemistry 2016 Volume 81(Issue 17) pp:7908-7916

Publication Date(Web):July 28, 2016

DOI:10.1021/acs.joc.6b01620

A photocatalytic decarboxylative/defluorinative reaction of α-trifluoromethyl alkenes with α-keto acids and α-amino acids has been developed. The reaction occurs at room temperature under visible light irradiation, affording various γ,γ-difluoroallylic ketones and 1,1-difluorohomoallyl amines in good yields. The synthetic applications of the resulting functionalized gem-difluoroalkenes were also described.

Regiospecific Synthesis of Benzoxepines through Pd-Catalyzed Carbene Migratory Insertion and C–C Bond Cleavage

Co-reporter:Yang Xie, Ping Zhang, and Lei Zhou

The Journal of Organic Chemistry 2016 Volume 81(Issue 5) pp:2128-2134

Publication Date(Web):February 4, 2016

DOI:10.1021/acs.joc.5b02413

A new method for the synthesis of benzoxepines via migratory insertion into a Pd carbene followed by C–C bond cleavage was developed. Various benzoxepines were constructed by the regioselective ring expansion concomitant with the introduction of an aryl group at their 5-position.

Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds

Co-reporter:Yong Liu;Xichang Dong;Guojun Deng

Science China Chemistry 2016 Volume 59( Issue 2) pp:199-202

Publication Date(Web):2016 February

DOI:10.1007/s11426-015-5513-8

A visible-light induced decarboxylative aza-Darzens reaction between N-aryl glycines and diazo compounds was developed, which affords various mono-substituted aziridines in good yields.

Ag(I)-Catalyzed Three-Component Reaction of 2-Alkynylbenzaldehydes, Amines, and Diazo Compounds

Co-reporter:Tiebo Xiao, Pai Peng, Yang Xie, Zhao-yang Wang, and Lei Zhou

Organic Letters 2015 Volume 17(Issue 17) pp:4332-4335

Publication Date(Web):August 26, 2015

DOI:10.1021/acs.orglett.5b02159

Diazo compounds have been employed as the nucleophile in a silver-catalyzed three-component reaction with amines and 2-alkynylbenzaldehydes. Various 3-benzazepines were prepared in a one-pot manner based on a cascade imine–-yne cyclization/nucleophilic addition/1,2-aryl migration process. Moreover, this Ag(I)-mediated reaction also provides a practical route to diazo-containing dihydroisoquinolines under slightly modified conditions.

Synthesis of Quinolines by Visible-Light Induced Radical Reaction of Vinyl Azides and -Carbonyl Benzyl Bromides

Co-reporter:Qile Wang;Jun Huang

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 11) pp:2479-2484

Publication Date(Web):

DOI:10.1002/adsc.201500141

Synthesis of 2-trifluoromethyl indoles via visible-light induced intramolecular radical cyclization

Co-reporter:Xichang Dong, Yumin Hu, Tiebo Xiao and Lei Zhou

RSC Advances 2015 vol. 5(Issue 49) pp:39625-39629

Publication Date(Web):27 Apr 2015

DOI:10.1039/C5RA05967D

A visible-light induced intramolecular radical cyclization of N-[2-(alkynyl)phenyl]trifluoroacetimidoyl chlorides is described. The reaction allows the rapid construction of diverse 2-trifluoromethyl-3-acylindoles in a sequential C–C and C–O bond formation process under mild conditions.

Synthesis of 6-substituted phenanthridines by metal-free, visible-light induced aerobic oxidative cyclization of 2-isocyanobiphenyls with hydrazines

Co-reporter:Tiebo Xiao, Linyong Li, Guoliang Lin, Qile Wang, Ping Zhang, Zong-wan Mao and Lei Zhou

Green Chemistry 2014 vol. 16(Issue 5) pp:2418-2421

Publication Date(Web):29 Jan 2014

DOI:10.1039/C3GC42517G

Irradiation of hydrazines with visible-light in the presence of organic dye eosin B generates various types of functional radicals, which are trapped by 2-isocyanobiphenyls to give 6-substituted phenanthridines.

Metal-Free Visible-Light Induced Cross-Dehydrogenative Coupling of Tertiary Amines with Diazo Compounds

Co-reporter:Tiebo Xiao, Linyong Li, Guoliang Lin, Zong-wan Mao, and Lei Zhou

Organic Letters 2014 Volume 16(Issue 16) pp:4232-4235

Publication Date(Web):July 30, 2014

DOI:10.1021/ol501933h

The first visible-light induced cross-dehydrogenative coupling between tertiary amines and diazo compounds is described. The reaction proceeds smoothly under mild and metal-free conditions by using air or O2 as the oxidant, affording various β-amino-α-diazo adducts in moderate to good yields with broad substrate scopes. The resulting products were successfully employed for the synthesis of 4- or 5-ester N-aryl-2,3-dihydrobenzo[d]azepines with high regioselectivity simply switched by the selection of the transition metal catalysts.

Synthesis of 3-Acylindoles by Visible-Light Induced Intramolecular Oxidative Cyclization of o-Alkynylated N,N-Dialkylamines

Co-reporter:Ping Zhang, Tiebo Xiao, Shengwei Xiong, Xichang Dong, and Lei Zhou

Organic Letters 2014 Volume 16(Issue 12) pp:3264-3267

Publication Date(Web):June 4, 2014

DOI:10.1021/ol501276j

A visible-light photoredox synthesis of 3-acylindoles through intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines is developed. The reaction proceeds effectively under mild reaction conditions using air as the oxidant, and only water is generated as a side product. A plausible mechanism involving the addition of α-amino alkyl radicals to alkynes, followed by C–O bond formation, is proposed.

CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: a general method for the synthesis of unsymmetrical propargylic acetals

Co-reporter:Tiebo Xiao, Ping Zhang, Yang Xie, Jun Wang and Lei Zhou

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 32) pp:6215-6222

Publication Date(Web):05 Jun 2014

DOI:10.1039/C4OB00614C

A general source of dialkoxycarbenes, 2,2-dialkoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazolines, have been successfully employed as coupling partners in CuI-catalyzed cross-coupling reactions with terminal alkynes, which afforded various unsymmetrical propargylic acetals in good yields.

PhI(OAc)2-Mediated Synthesis of 6-(Trifluoromethyl)phenanthridines by Oxidative Cyclization of 2-Isocyanobiphenyls with CF3SiMe3 under Metal-Free Conditions

Co-reporter:Qile Wang, Xichang Dong, Tiebo Xiao, and Lei Zhou

Organic Letters 2013 Volume 15(Issue 18) pp:4846-4849

Publication Date(Web):September 3, 2013

DOI:10.1021/ol4022589

A mild and efficient method for the synthesis of 6-(trifluoromethyl)phenanthridines through oxidative cyclization of 2-isocyanobiphenyls with CF3SiMe3 under metal-free conditions was developed. The reaction allows the direct formation of C–CF3 bonds and rapid access to phenanthridine ring systems in one catalytic cycle.

Benzofuran and indole synthesis via Cu(I)-catalyzed coupling of N-tosylhydrazone and o-hydroxy or o-amino phenylacetylene

Co-reporter:Tiebo Xiao, Xichang Dong and Lei Zhou

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 9) pp:1490-1497

Publication Date(Web):30 Oct 2012

DOI:10.1039/C2OB26867A

A general and practical method to synthesize 2-substituted benzofurans and indoles is described. This method employs easily accessible N-tosylhydrazones and o-hydroxy or o-amino phenylacetylenes as substrates. The reaction proceeds through a CuBr-catalyzed coupling–allenylation–cyclization sequence under ligand-free conditions.

Copper-catalyzed synthesis of benzazoles via aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines

Co-reporter:Tiebo Xiao, Shengwei Xiong, Yang Xie, Xichang Dong and Lei Zhou

RSC Advances 2013 vol. 3(Issue 36) pp:15592-15595

Publication Date(Web):15 Jul 2013

DOI:10.1039/C3RA42175A

A simple and efficient method for the synthesis of benzazoles via Cu-catalyzed aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines was developed.

Visible-Light-Induced Radical Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes: Catalytic Synthesis of 2-Trifluoromethyl Quinolines

Co-reporter:Xichang Dong;Youwei Xu;Jing Jing Liu;Yumin Hu;Tiebo Xiao ;Dr. Lei Zhou

Chemistry - A European Journal 2013 Volume 19( Issue 50) pp:16928-16933

Publication Date(Web):

DOI:10.1002/chem.201303149

Phenanthrene Synthesis by Eosin Y-Catalyzed, Visible Light- Induced [4+2]Benzannulation of Biaryldiazonium Salts with Alkynes

Co-reporter:Tiebo Xiao;Xichang Dong;Yanchi Tang

Advanced Synthesis & Catalysis 2012 Volume 354( Issue 17) pp:3195-3199

Publication Date(Web):

DOI:10.1002/adsc.201200569

Abstract

A metal-free, visible light-induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety of 9-substituted or 9,10-disubstituted phenanthrenes were obtained via a cascade radical addition and cyclization sequence.

Cobalt-catalyzed alkyne–dihalomethane–amine coupling: an efficient route for propargylamines

Co-reporter:Yanchi Tang, Tiebo Xiao, Lei Zhou

Tetrahedron Letters 2012 Volume 53(Issue 46) pp:6199-6201

Publication Date(Web):14 November 2012

DOI:10.1016/j.tetlet.2012.08.136

A cobalt-catalyzed three-component coupling of terminal alkynes, dihalomethanes, and amines was developed. This method offers an efficient way for propargylamines via the dual activation of C–H and C–halogen bond. The reaction uses cheap CoBr2 as catalyst and is phosphine ligand-free. A wide range of functional groups were found to tolerate the reaction conditions.

Benzofuran and indole synthesis via Cu(I)-catalyzed coupling of N-tosylhydrazone and o-hydroxy or o-amino phenylacetylene

Co-reporter:Tiebo Xiao, Xichang Dong and Lei Zhou

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 9) pp:NaN1497-1497

Publication Date(Web):2012/10/30

DOI:10.1039/C2OB26867A

CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: a general method for the synthesis of unsymmetrical propargylic acetals

Co-reporter:Tiebo Xiao, Ping Zhang, Yang Xie, Jun Wang and Lei Zhou

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 32) pp:NaN6222-6222

Publication Date(Web):2014/06/05

DOI:10.1039/C4OB00614C

Silver-catalyzed geminal aminofluorination of diazoketones with anilines and N-fluorobenzenesulphonimide

Co-reporter:Jun Huang, Linyong Li, Haoguo Chen, Tiebo Xiao, Yuwei He and Lei Zhou