TY - JOUR
T1 - Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes
AU - Song, Shengjin
AU - Liu, Huan
AU - Wang, Lu
AU - Zhu, Chuan
AU - Loh, Teck Peng
AU - Feng, Chao
N1 - Publisher Copyright:
© 2019 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/10/1
Y1 - 2019/10/1
N2 - Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.
AB - Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.
UR - http://www.scopus.com/inward/record.url?scp=85072074109&partnerID=8YFLogxK
U2 - 10.1002/cjoc.201900197
DO - 10.1002/cjoc.201900197
M3 - 文章
AN - SCOPUS:85072074109
SN - 1001-604X
VL - 37
SP - 1036
EP - 1040
JO - Chinese Journal of Chemistry
JF - Chinese Journal of Chemistry
IS - 10
ER -