Nickel-Catalyzed Cross-Electrophile Coupling Reactions for the Synthesis of gem-Difluorovinyl Arenes

被引：49

作者：

Xiong, Baojian ^{[1
,2
,3
]}

Wang, Ting ^{[4
]}

Sun, Haotian ^{[1
,2
,3
]}

Li, Yue ^{[1
,2
,3
]}

Kramer, Soren ^{[5
]}

Cheng, Gui-Juan ^{[4
]}

Lian, Zhong ^{[1
,2
,3
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Dermatol, Chengdu 610041, Peoples R China

[2] Sichuan Univ, West China Hosp, Canc Ctr, Chengdu 610041, Peoples R China

[3] Sichuan Univ, West China Sch Pharm, Chengdu 610041, Peoples R China

[4] Chinese Univ Hong Kong Shenzhen, Sch Life & Hlth Sci, Shenzhen Key Lab Steroid Drug Dev, Warshel Inst Computat Biol, Shenzhen 518172, Peoples R China

[5] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

来源：

ACS CATALYSIS | 2020年 / 10卷 / 22期

关键词：

nickel catalysis; cross-electrophile coupling; gem-difluoroalkenes; 2,2-difluorovinyl tosylate; DFT studies; DIFLUOROMETHYL 2-PYRIDYL SULFONE; LIGHT-EMITTING-DIODES; C-O ACTIVATION; AROMATIC-ALDEHYDES; DIFLUOROALKENES; ALKENES; DIFLUOROOLEFINATION; CONSTRUCTION; AMIDATION; HALIDES;

D O I：

10.1021/acscatal.0c03993

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A nickel-catalyzed cross-electrophile coupling reaction between (hetero)aryl bromides and 2,2-difluorovinyl tosylate is presented. This protocol provides facile incorporation of the gem-difluorovinyl moiety in organic molecules. The method features mild reaction conditions, good functional group tolerance, and excellent yields. Furthermore, mechanistic experiments and DFT studies indicate a Ni(0)/Ni(II) catalytic cycle, thus differing from the currently accepted catalytic cycle for nickel-catalyzed C(sp(2))-C(sp(2)) cross-electrophile coupling reactions.

引用

页码：13616 / 13623

页数：8

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