Copper(I)-catalyzed borylative exo -cyclization of alkenyl halides containing unactivated double bond

Koji Kubota; Eiji Yamamoto; Hajime Ito

doi:10.1021/ja3104582

Copper(I)-catalyzed borylative exo -cyclization of alkenyl halides containing unactivated double bond

Koji Kubota, Eiji Yamamoto, Hajime Ito

Research output: Contribution to journal › Article › peer-review

167 Citations (Scopus)

Abstract

A borylative exo-cyclization of alkenyl halides has been reported. The reaction includes the regioselective addition of a borylcopper(I) intermediate to unactivated terminal alkenes, followed by the intramolecular substitution of the resulting alkylcopper(I) moiety for the halide leaving groups. Experimental and theoretical investigations of the reaction mechanism have also been described. This reaction provides a new method for the synthesis of alkylboronates containing strained cycloalkyl structures from simple starting materials.

Original language	English
Pages (from-to)	2635-2640
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	135
Issue number	7
DOIs	https://doi.org/10.1021/ja3104582
Publication status	Published - Feb 20 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja3104582

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abstract = "A borylative exo-cyclization of alkenyl halides has been reported. The reaction includes the regioselective addition of a borylcopper(I) intermediate to unactivated terminal alkenes, followed by the intramolecular substitution of the resulting alkylcopper(I) moiety for the halide leaving groups. Experimental and theoretical investigations of the reaction mechanism have also been described. This reaction provides a new method for the synthesis of alkylboronates containing strained cycloalkyl structures from simple starting materials.",

author = "Koji Kubota and Eiji Yamamoto and Hajime Ito",

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AU - Kubota, Koji

AU - Yamamoto, Eiji

AU - Ito, Hajime

PY - 2013/2/20

Y1 - 2013/2/20

N2 - A borylative exo-cyclization of alkenyl halides has been reported. The reaction includes the regioselective addition of a borylcopper(I) intermediate to unactivated terminal alkenes, followed by the intramolecular substitution of the resulting alkylcopper(I) moiety for the halide leaving groups. Experimental and theoretical investigations of the reaction mechanism have also been described. This reaction provides a new method for the synthesis of alkylboronates containing strained cycloalkyl structures from simple starting materials.

AB - A borylative exo-cyclization of alkenyl halides has been reported. The reaction includes the regioselective addition of a borylcopper(I) intermediate to unactivated terminal alkenes, followed by the intramolecular substitution of the resulting alkylcopper(I) moiety for the halide leaving groups. Experimental and theoretical investigations of the reaction mechanism have also been described. This reaction provides a new method for the synthesis of alkylboronates containing strained cycloalkyl structures from simple starting materials.

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JF - Journal of the American Chemical Society

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ER -

Copper(I)-catalyzed borylative exo -cyclization of alkenyl halides containing unactivated double bond

Abstract

All Science Journal Classification (ASJC) codes

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