Palladium‐Catalyzed Regioselective Three‐Component Cascade Bisthiolation of Terminal Alkynes

Jianxiao Li; Lu Ouyang; Shaorong Yang

doi:10.1002/adsc.201701417

journal article Jan 30, 2018

Palladium‐Catalyzed Regioselective Three‐Component Cascade Bisthiolation of Terminal Alkynes

Jianxiao Li Lu Ouyang Shaorong Yang

Advanced Synthesis & Catalysis Vol. 360 No. 6 pp. 1138-1150 · Wiley

View at Publisher Save 10.1002/adsc.201701417

Abstract

AbstractAn efficient and novel NHC(N‐heterocyclic carbene)‐palladium‐catalyzed three‐component cascade bisthiolation of terminal alkynes, K2S (potassium sulfide) and diaryliodonium salts for the assembly of functionalized (Z)‐1,2‐bis(arylthio)alkene derivatives has been accomplished for the first time. This unique observation features a broad substrate scope, excellent functional‐group tolerance, and high regioselectivity. Especially, an arylthiolate anion from diaryliodonium salts and potassium sulfide was proposed as the key intermediate in the catalytic cycle.magnified image

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References

90

[1]

For selected reviews

[2]

Synthesis of Heterocycles via Electrophilic Cyclization of Alkynes Containing Heteroatom

Benhur Godoi, Ricardo F. Schumacher, Gilson Zeni

Chemical Reviews 10.1021/cr100214d

[3]

10.1016/j.tetlet.2014.05.077

[4]

B. M. Trost C.-J. Li Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations. Wiley-VCH Weinheim 2014; 10.1002/9783527677894

[5]

10.1021/cr400133p

[6]

10.1021/acs.chemrev.5b00514

[7]

10.1002/chem.201603044

[8]

For selected reviews

[9]

10.1002/1521-3765(20020617)8:12<2660::aid-chem2660>3.0.co;2-q

[10]

10.1002/ejoc.201403507

[11]

10.1021/acscatal.5b02973

[12]

For selected reviews

[13]

10.1021/cr9902594

[14]

10.1021/cr050530j

[15]

10.1021/cr3003517

[16]

10.1021/ja00069a020

[17]

10.1021/acs.orglett.6b00503

[18]

10.1021/acscatal.6b00127

[19]

10.1002/adsc.201600883

[20]

For selected reviews

[21]

A. Ding H. Guo Comprehensive Organic Synthesis 2nd ed. Elsevier Oxford 2014;

[22]

10.1039/c4cs00304g

[23]

10.1002/chem.201603044

[24]

For selected examples

[25]

10.1021/ja4052685

[26]

10.1002/anie.201402511

[27]

Pd-Catalyzed Stereoselective Carboperfluoroalkylation of Alkynes

Zhaodong Li, Andrés García-Domínguez, Cristina Nevado

Journal of the American Chemical Society 10.1021/jacs.5b07432

[28]

10.1021/acs.orglett.5b02512

[29]

10.1002/anie.201601296

[30]

10.1021/acscatal.6b02039

[31]

[32]

10.1016/j.tetlet.2009.03.101

[33]

10.1038/nature14061

[34]

10.1016/j.apcata.2017.05.024

[35]

[36]

10.1016/j.bmcl.2007.02.003

[37]

10.1016/j.bmcl.2011.10.099

[38]

10.1002/cbdv.201700296

[39]

[40]

10.1021/ja00026a013

[41]

10.1039/b312471a

[42]

10.1055/s-2005-865195

[43]

10.1039/b706320b

[44]

10.1021/ol015521l

[45]

10.1002/chem.200701278

[46]

10.1080/00397910802654831

[47]

10.1021/acscatal.5b01815

[48]

[49]

10.1002/anie.201311217

[50]

10.1039/c4gc00542b

Showing 50 of 90 references

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Details

Published: Jan 30, 2018
Vol/Issue: 360(6)
Pages: 1138-1150
License: View

Authors

J

Jianxiao Li

Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 People's Republic of China

L

Lu Ouyang

Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 People's Republic of China

S

Shaorong Yang

Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 People's Republic of China

Funding

National Natural Science Foundation of China Award: 21502055

Cite This Article

Jianxiao Li, Lu Ouyang, Shaorong Yang (2018). Palladium‐Catalyzed Regioselective Three‐Component Cascade Bisthiolation of Terminal Alkynes. Advanced Synthesis & Catalysis, 360(6), 1138-1150. https://doi.org/10.1002/adsc.201701417

Palladium‐Catalyzed Regioselective Three‐Component Cascade Bisthiolation of Terminal Alkynes

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