Nickel Catalyzed Cross-Coupling of Aryl and Alkenyl Triflates with Alkyl Thiols

被引：17

作者：

Oechsner, Regina M. ^{[1
]}

Lindenmaier, Ivo H. ^{[1
]}

Fleischer, Ivana ^{[1
]}

机构：

[1] Eberhard Karls Univ Tubingen, Inst Organ Chem, Fac Sci, D-72076 Tubingen, Germany

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 10期

关键词：

C-N; HALIDES; SULFIDES; TRANSFORMATION; CONVERSION; CHLORIDES; COMPLEXES; ARYLATION; BROMIDES; ROUTE;

D O I：

10.1021/acs.orglett.3c00218

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a nickel catalyzed C-S cross-coupling of aryl and alkenyl triflates with alkyl thiols. A variety of the corresponding thioethers were synthesized using an air-stable nickel precatalyst under mild reaction conditions with short reaction times. A broad substrate scope, including pharmaceutically relevant compounds, could be demonstrated.

引用

页码：1655 / 1660

页数：6

共 57 条

[1] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[2]

Collins C. J., 1984, ANGEW CHEM INT EDIT, V117, P2815

[3] Chemical routes for the transformation of biomass into chemicals [J].

Corma, Avelino ;

Iborra, Sara ;

Velty, Alexandra .

CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502

[4]

CRISTAU HJ, 1981, SYNTHESIS-STUTTGART, P892

[5] Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides [J].

Duan, Jicheng ;

Du, Yun-Fei ;

Pang, Xiaobo ;

Shu, Xing-Zhong .

CHEMICAL SCIENCE, 2019, 10 (37) :8706-8712

[6] A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].

Fernández-Rodríguez, MA ;

Shen, QL ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181

[7] Cross-Coupling of Chloro(hetero)arenes with Thiolates Employing a Ni(0)-Precatalyst [J].

Gehrtz, Paul H. ;

Geiger, Valentin ;

Schmidt, Tanno ;

Srsan, Laura ;

Fleischer, Ivana .

ORGANIC LETTERS, 2019, 21 (01) :50-55

[8] Nickel-Catalyzed Coupling of Arylzinc Halides with Thioesters [J].

Gehrtz, Paul H. ;

Kathe, Prasad ;

Fleischer, Ivana .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (35) :8774-8778

[9] Recent Metal-Catalyzed Methods for Thioether Synthesis [J].

Geiger, Valentin J. ;

Oechsner, Regina M. ;

Gehrtz, Paul H. ;

Fleischer, Ivana .

SYNTHESIS-STUTTGART, 2022, 54 (23) :5139-5167

[10] Decarboxylative Biaryl Synthesis from Aromatic Carboxylates and Aryl Triflates [J].

Goossen, Lukas J. ;

Rodriguez, Nuria ;

Linder, Christophe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (46) :15248-+

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