Nickel-Catalyzed Cross-Electrophile Coupling Reactions between Allylic Acetates and gem-Difluorovinyl Tosylate

被引：4

作者：

He, Xiaochun ^{[1
,2
,3
]}

Liu, Jiangjun ^{[1
,2
,3
]}

Chen, Gang ^{[1
,2
,3
]}

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

Xiao, Xue ^{[1
,2
,3
]}

Chen, Lei ^{[1
,2
,3
]}

Zhang, Xuemei ^{[1
,2
,3
]}

Dong, Lin ^{[1
,2
,3
]}

Ma, Xuelei ^{[1
,2
,3
]}

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

机构：

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

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

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

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 19期

基金：

中国国家自然科学基金;

关键词：

DIAZO-COMPOUNDS; DIFLUOROOLEFINATION; GENERATION; HALIDES; TMSCF3; ZINC;

D O I：

10.1021/acs.orglett.2c01245

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel-catalyzed cross-electrophile coupling of allylic acetates and gem-difluorovinyl tosylate is presented, which first achieves allylic gem-difluoroolefins via C(sp(3))-C(sp(2)) cross-electrophile coupling. In addition, this protocol was performed under mild reaction conditions, affording a variety of allylic gem-difluorovinyl arenes in moderate to good yields. Moreover, both linear and branched allylic acetate could produce a linear cross-coupling product exclusively. Mechanistic studies reveal that the reaction involves two different Ni(0)/Ni(II) catalytic cycles.

引用

页码：3538 / 3543

页数：6

共 40 条

[1] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[2] Fluorinated ylides and related compounds [J].

Burton, DJ ;

Yang, ZY ;

Qiu, WM .

CHEMICAL REVIEWS, 1996, 96 (05) :1641-1715

[3] Remote Migratory Cross-Electrophile Coupling and Olefin Hydroarylation Reactions Enabled by in Situ Generation of NiH [J].

Chen, Fenglin ;

Chen, Ke ;

Zhang, Yao ;

He, Yuli ;

Wang, Yi-Ming ;

Zhu, Shaolin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (39) :13929-13935

[4] 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions [J].

Du, Bingnan ;

Chan, Chun-Ming ;

Lee, Pui-Yiu ;

Cheung, Leong-Hung ;

Xu, Xin ;

Lin, Zhenyang ;

Yu, Wing-Yiu .

NATURE COMMUNICATIONS, 2021, 12 (01)

[5] Fluorinated butatrienes [J].

Ehm, Christian ;

Akkerman, Floris A. ;

Lentz, Dieter .

JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (11) :1173-1181

[6] Facile Synthesis of β,β-Difluorostyrenes via the Negishi Coupling of Thermally Stable 2,2-Difluorovinyl Zinc-TMEDA Complex [J].

Fujita, Takeshi ;

Ichitsuka, Tomohiro ;

Fuchibe, Kohei ;

Ichikawa, Junji .

CHEMISTRY LETTERS, 2011, 40 (09) :986-988

[7] Difluoromethyl 2-pyridyl sulfone: a versatile carbonyl gem-difluoroolefination reagent [J].

Gao, Bing ;

Zhao, Yanchuan ;

Hu, Jingyu ;

Hu, Jinbo .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (02) :163-168

[8] Direct vinylation and difluorovinylation of arylboronic acids using vinyl- and 2,2-difluorovinyl tosylates via the Suzuki-Miyaura cross coupling [J].

Gogsig, Thomas M. ;

Sobjerg, Lina S. ;

Lindhardt , Anders T. ;

Jensen, Kim L. ;

Skrydstrup, Troels .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3404-3410

[9] Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations [J].

Gu, Jun ;

Wang, Xuan ;

Xue, Weichao ;

Gong, Hegui .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1411-1421

[10] Visible-Light-Induced Deoxygenation/Defluorination Protocol for Synthesis of γ,γ-Difluoroallylic Ketones [J].

Guo, Yuan-Qiang ;

Wang, Ruiguo ;

Song, Hongjian ;

Liu, Yuxiu ;

Wang, Qingmin .

ORGANIC LETTERS, 2020, 22 (02) :709-713

← 1 2 3 4 →