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Electrophilic Borylation of Terminal Alkenes with BBr3/2,6-Disubstituted Pyridines.

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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… Click to show full 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.

Keywords: bbr3 disubstituted; terminal; borylation terminal; electrophilic borylation; alkenes bbr3; terminal alkenes

Journal Title: Organic letters
Year Published: 2018

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