Electrophilic borylation of terminal alkenes with BBr3/2,6-disubstituted pyridines

Shinya Tanaka; Yuki Saito; Takaya Yamamoto; Tetsutaro Hattori

doi:10.1021/acs.orglett.8b00335

Electrophilic borylation of terminal alkenes with BBr₃/2,6-disubstituted pyridines

Shinya Tanaka, Yuki Saito, Takaya Yamamoto, Tetsutaro Hattori

工学研究科・バイオ工学専攻

研究成果: Article › 査読

24 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	1828-1831
ページ数	4
ジャーナル	Organic letters
巻	20
号	7
DOI	https://doi.org/10.1021/acs.orglett.8b00335
出版ステータス	Published - 2018 4月 6

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

文献へのアクセス

10.1021/acs.orglett.8b00335

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引用スタイル

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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.",

author = "Shinya Tanaka and Yuki Saito and Takaya Yamamoto and Tetsutaro Hattori",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number K17K144430. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Hattori, Tetsutaro

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AB - 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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