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Electrophilic Borylation of Terminal Alkenes with BBr3/2,6-Disubstituted Pyridines
Shinya Tanaka1, Yuki Saito1, Takaya Yamamoto1
1Department of Biomolecular Engineering, Graduate School of Engineering , Tohoku University , 6-6-11 Aramaki-Aoba , Aoba-ku , Sendai 980-8579 , Japan.
Abstract:
A variety of terminal alkenes, as well as heteroaromatic compounds, are borylated by the combined use of BBr3/2,6-dichloropyridine (B3) or BBr3/2,6-lutidine (B5). α,α-Diarylalkenes prefer the former reagent combination, while other alkenes prefer the latter. Mechanistic considerations strongly suggest that the former and latter reactions proceed through electrophilic substitution reactions with BBr3 and [BBr2·B5]+BBr4-, respectively.
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