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Copper(I)‐Promoted Alkylation of Alkenylbenzyldimethylsilanes
Author(s) -
Takeda Takeshi,
Matsumura Ryo,
Wasa Hideki,
Tsubouchi Akira
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402060
Subject(s) - chemistry , electrophile , halide , aryl , heteroatom , alkylation , alkyl , medicinal chemistry , palladium , copper , base (topology) , coupling (piping) , coupling reaction , catalysis , organic chemistry , mechanical engineering , mathematical analysis , mathematics , engineering
Palladium‐catalyzed cross‐coupling of acid‐ and base‐unstable heteroatom‐functionalized organosilanes and C(sp 2 )X electrophiles such as aryl and alkenyl (pseudo)halides has been extensively studied. In contrast, little is known about the coupling between unactivated alkenyltrialkylsilanes and C(sp 3 )X electrophiles. Herein, the copper(I)‐promoted coupling of chromatographically stable alkenylbenzyldimethylsilanes with unreactive alkyl halides as well as allyl and benzyl halides is described. The reaction proceeds in the presence of CuI‐P(OEt) 3 and Bu 4 NF ⋅ ( t BuOH) 4 to produce stereodefined di‐ and trisubstituted alkenes with complete retention of configuration.