Photoinduced Copper-Catalyzed Site-Selective C(sp2)-C(sp) Cross-Coupling via Aryl Sulfonium Salts

被引：51

作者：

Liang, Lei ^{[1
]}

Niu, Hong-Ying ^{[1
]}

Li, Ren-Long ^{[1
]}

Wang, Yao-Fei ^{[1
]}

Yan, Jin-Kai ^{[1
]}

Li, Chang-Gong ^{[1
]}

Guo, Hai-Ming ^{[2
]}

机构：

[1] Henan Inst Sci & Technol, Sch Chem & Chem Engn, Xinxiang 453003, Henan, Peoples R China

[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 17期

基金：

中国国家自然科学基金;

关键词：

SONOGASHIRA REACTION; REDUCTION; LIGHT;

D O I：

10.1021/acs.orglett.0c02364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The classical Sonogashira reaction of aryl electrophiles in the presence of Pd catalysts has been well established as a potent method for arylalkyne synthesis. However, the site-selective C(sp(2))-C(sp) cross-coupling strategy using a non-noble-metal catalyst is rare. An efficient alternative approach for the synthesis of arylalkynes via a Cu-catalyzed Sonogashira-type reaction promoted by visible light is described. This method enables site-selective alkynylation from aryl sulfonium salts derived from diverse arenes to a set of arylalkynes with high selectivity and high functional-group compatibility. Moreover, rapid alkynylation of drug molecules is demonstrated.

引用

页码：6842 / 6846

页数：5

共 44 条

[1] Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides [J].

Alvarez, Eva Maria ;

Plutschack, Matthew B. ;

Berger, Florian ;

Ritter, Tobias .

ORGANIC LETTERS, 2020, 22 (12) :4593-4596

[2] Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation [J].

Aukland, Miles H. ;

Siauciulis, Mindaugas ;

West, Adam ;

Perry, Gregory J. P. ;

Procter, David J. .

NATURE CATALYSIS, 2020, 3 (02) :163-169

[3] Thiopeptide antibiotics [J].

Bagley, MC ;

Dale, JW ;

Merritt, EA ;

Xiong, A .

CHEMICAL REVIEWS, 2005, 105 (02) :685-714

[4] Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].

Berger, Florian ;

Plutschack, Matthew B. ;

Riegger, Julian ;

Yu, Wanwan ;

Speicher, Samira ;

Ho, Matthew ;

Frank, Nils ;

Ritter, Tobias .

NATURE, 2019, 567 (7747) :223-228

[5] Iron-catalyzed Sonogashira reactions [J].

Carril, Monica ;

Correa, Arkaitz ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4862-4865

[6] Sonogashira Cross-Coupling of Aryltrimethylammonium Salts [J].

Chen, Qianwei ;

Gao, Fengchen ;

Tang, Huiling ;

Yao, Miao ;

Zhao, Qan ;

Shi, Yanhui ;

Dang, Yanfeng ;

Cao, Changsheng .

ACS CATALYSIS, 2019, 9 (04) :3730-3736

[7] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[8]

Diederich F, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, pV

[9] Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals [J].

Donck, Simon ;

Baroudi, Abdulkader ;

Fensterbank, Louis ;

Goddard, Jean-Philippe ;

Ollivier, Cyril .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) :1477-1482

[10] C-N Cross-Couplings for Site-Selective Late-Stage Diversification via Aryl Sulfonium Salts [J].

Engl, Pascal S. ;

Haering, Andreas P. ;

Berger, Florian ;

Berger, Georg ;

Perez-Bitrian, Alberto ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (34) :13346-13351

← 1 2 3 4 5 →