Nickel-Catalyzed Stereoselective Cascade C-F Functionalizations of gem-Difluoroalkenes

被引：15

作者：

Li, Xiaowei ^{[1
]}

Li, Yuxiu ^{[1
,2
]}

Wang, Zemin ^{[1
]}

Shan, Wenlong ^{[1
]}

Liu, Ruihua ^{[1
]}

Shi, Cong ^{[1
]}

Qin, Hongyun ^{[1
]}

Yuan, Leifeng ^{[1
]}

Li, Xiangqian ^{[1
]}

Shi, Dayong ^{[1
,3
]}

机构：

[1] Shandong Univ, State Key Lab Microbial Technol, Qingdao 266237, Shandong, Peoples R China

[2] Jiaying Univ, Sch Chem & Environm, Meizhou 514015, Guangdong, Peoples R China

[3] Pilot Natl Lab Marine Sci & Technol, Lab Marine Drugs & Biol Prod, Qingdao 266237, Shandong, Peoples R China

来源：

ACS CATALYSIS | 2023年 / 13卷 / 03期

关键词：

dual C-F functionalization; reductive cross-couplings; nickel; gem-di?uoroalkenes; 1; 3-dienes; deuteration; CROSS-COUPLING REACTIONS; BOND ACTIVATION; CHEMISTRY; BORYLATION; 1,3-DIENES; MOLECULES; DEUTERIUM; SECONDARY; TERTIARY; HALIDES;

D O I：

10.1021/acscatal.3c00047

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：

The activation and functionalization of C-F bonds for the construction of C-C and C-X bonds have drawn significant research attention in recent years. However, the chemo-and stereoselective control of dual C-F bond functionalization of gem-difluoroalkenes remains a formidable challenge. Herein, a Ni-catalyzed reductive cross-coupling of gem-difluoroalkenes with alkenyl-electrophiles and D2O that allowed the generation of C(sp2)-C(sp2) bonds and C(sp2)-D bonds in one pot by successive defluorination is described. This methodology offers facile access to various deuterated 1,3-dienes with broad functional group compatibility and (E)-selectivity under mild conditions. Preliminary mechanistic studies indicate that alpha-alkenyl-substituted monofluoroalkenes might be intermediates in this protocol.

引用

页码：2135 / 2141

页数：7

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