Copper(I)‐Promoted Alkylation of Alkenylbenzyldimethylsilanes | Zendy

Takeda Takeshi | Zendy; Matsumura Ryo | Zendy; Wasa Hideki | Zendy; Tsubouchi Akira | Zendy

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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.

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