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Rhodium‐Catalyzed Defluorinative Vinylation of gem ‐Difluoroalkenes for the Synthesis of 2‐Fluoro‐1,3‐dienes
Author(s) -
Song Shengjin,
Liu Huan,
Wang Lu,
Zhu Chuan,
Loh TeckPeng,
Feng Chao
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900197
Subject(s) - chemistry , rhodium , stereoselectivity , catalysis , reactivity (psychology) , halide , nucleophile , diene , medicinal chemistry , fluorine , combinatorial chemistry , organic chemistry , stereochemistry , medicine , natural rubber , alternative medicine , pathology
Summary of main observation and conclusion Herein, we present a strategy for the formation of 2‐fluoro‐1,3‐diene derivatives via rhodium‐catalyzed direct C(sp 2 )—C(sp 2 ) cross‐coupling of gem ‐difluoroalkenes and acrylamides. By merging Rh(III)‐catalyzed C(sp 2 )–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.