Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes

Takashi Kippo; Kanako Hamaoka; Mitsuhiro Ueda; Takahide Fukuyama; Ilhyong Ryu

doi:10.1016/j.tet.2016.05.084

Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes

Takashi Kippo
, Kanako Hamaoka
, Mitsuhiro Ueda
, Takahide Fukuyama
, Ilhyong Ryu^*

^*此作品的通信作者

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14 引文斯高帕斯（Scopus）

摘要

The full scope (30 examples) of the radical bromoallylation of alkynes using allyl bromides was studied. In this reaction, bromine radical adds to alkynes to form vinyl radicals, which then undergo an S_H2′ reaction with allyl bromides to produce good yields of 1-bromo-1,4-dienes with the liberation of a bromine radical, which creates a radical chain. The sp²-carbon–bromine bond of the product dienes was further functionalized via cross-coupling and carbonylation reactions.

原文	English
頁（從 - 到）	7866-7874
頁數	9
期刊	Tetrahedron
卷	72
發行號	48
DOIs	https://doi.org/10.1016/j.tet.2016.05.084
出版狀態	Published - 2016

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10.1016/j.tet.2016.05.084

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title = "Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes",

abstract = "The full scope (30 examples) of the radical bromoallylation of alkynes using allyl bromides was studied. In this reaction, bromine radical adds to alkynes to form vinyl radicals, which then undergo an SH2′ reaction with allyl bromides to produce good yields of 1-bromo-1,4-dienes with the liberation of a bromine radical, which creates a radical chain. The sp2-carbon–bromine bond of the product dienes was further functionalized via cross-coupling and carbonylation reactions.",

keywords = "Alkynes, Allyl bromides, Bromoallylation, Dienes, Radical reaction",

author = "Takashi Kippo and Kanako Hamaoka and Mitsuhiro Ueda and Takahide Fukuyama and Ilhyong Ryu",

note = "Publisher Copyright: {\textcopyright} 2016",

year = "2016",

doi = "10.1016/j.tet.2016.05.084",

language = "English",

volume = "72",

pages = "7866--7874",

journal = "Tetrahedron",

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T1 - Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes

AU - Kippo, Takashi

AU - Hamaoka, Kanako

AU - Ueda, Mitsuhiro

AU - Fukuyama, Takahide

AU - Ryu, Ilhyong

PY - 2016

Y1 - 2016

N2 - The full scope (30 examples) of the radical bromoallylation of alkynes using allyl bromides was studied. In this reaction, bromine radical adds to alkynes to form vinyl radicals, which then undergo an SH2′ reaction with allyl bromides to produce good yields of 1-bromo-1,4-dienes with the liberation of a bromine radical, which creates a radical chain. The sp2-carbon–bromine bond of the product dienes was further functionalized via cross-coupling and carbonylation reactions.

AB - The full scope (30 examples) of the radical bromoallylation of alkynes using allyl bromides was studied. In this reaction, bromine radical adds to alkynes to form vinyl radicals, which then undergo an SH2′ reaction with allyl bromides to produce good yields of 1-bromo-1,4-dienes with the liberation of a bromine radical, which creates a radical chain. The sp2-carbon–bromine bond of the product dienes was further functionalized via cross-coupling and carbonylation reactions.

KW - Alkynes

KW - Allyl bromides

KW - Bromoallylation

KW - Dienes

KW - Radical reaction

UR - https://www.scopus.com/pages/publications/84977570927

U2 - 10.1016/j.tet.2016.05.084

DO - 10.1016/j.tet.2016.05.084

M3 - Article

AN - SCOPUS:84977570927

SN - 0040-4020

VL - 72

SP - 7866

EP - 7874

JO - Tetrahedron

JF - Tetrahedron

IS - 48

ER -

Radical bromoallylation of alkynes leading to 1-bromo-1,4-dienes

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