Bromoallylation of alkenes leading to 4-alkenyl bromides based on trapping of β-bromoalkyl radicals

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

doi:10.1021/acs.orglett.7b02471

Bromoallylation of alkenes leading to 4-alkenyl bromides based on trapping of β-bromoalkyl radicals

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

^*Corresponding author for this work

Department of Applied Chemistry

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

7 Scopus citations

Abstract

A radical-chain addition of allyl bromides to aryl alkenes, vinyl ester, and vinyl phthalimide was studied in which elusive β-bromoalkyl radicals were trapped efficiently to give 5-bromo-1-pentenes in good to high yields (16 examples). A subsequent carbonylative radical cyclization with AIBN/Bu₃SnH/CO was successful in giving the corresponding 3,5-disubstituted cyclohexanone derivatives in moderate yields. Synthesis of a piperidine ring was also successful by subsequent reaction with primary amine.

Original language	English
Pages (from-to)	5198-5200
Number of pages	3
Journal	Organic Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02471
State	Published - 6 Oct 2017

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title = "Bromoallylation of alkenes leading to 4-alkenyl bromides based on trapping of β-bromoalkyl radicals",

abstract = "A radical-chain addition of allyl bromides to aryl alkenes, vinyl ester, and vinyl phthalimide was studied in which elusive β-bromoalkyl radicals were trapped efficiently to give 5-bromo-1-pentenes in good to high yields (16 examples). A subsequent carbonylative radical cyclization with AIBN/Bu3SnH/CO was successful in giving the corresponding 3,5-disubstituted cyclohexanone derivatives in moderate yields. Synthesis of a piperidine ring was also successful by subsequent reaction with primary amine.",

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

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doi = "10.1021/acs.orglett.7b02471",

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T1 - Bromoallylation of alkenes leading to 4-alkenyl bromides based on trapping of β-bromoalkyl radicals

AU - Kippo, Takashi

AU - Hamaoka, Kanako

AU - Ueda, Mitsuhiro

AU - Fukuyama, Takahide

AU - Ryu, Ilhyong

PY - 2017/10/6

Y1 - 2017/10/6

N2 - A radical-chain addition of allyl bromides to aryl alkenes, vinyl ester, and vinyl phthalimide was studied in which elusive β-bromoalkyl radicals were trapped efficiently to give 5-bromo-1-pentenes in good to high yields (16 examples). A subsequent carbonylative radical cyclization with AIBN/Bu3SnH/CO was successful in giving the corresponding 3,5-disubstituted cyclohexanone derivatives in moderate yields. Synthesis of a piperidine ring was also successful by subsequent reaction with primary amine.

AB - A radical-chain addition of allyl bromides to aryl alkenes, vinyl ester, and vinyl phthalimide was studied in which elusive β-bromoalkyl radicals were trapped efficiently to give 5-bromo-1-pentenes in good to high yields (16 examples). A subsequent carbonylative radical cyclization with AIBN/Bu3SnH/CO was successful in giving the corresponding 3,5-disubstituted cyclohexanone derivatives in moderate yields. Synthesis of a piperidine ring was also successful by subsequent reaction with primary amine.

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U2 - 10.1021/acs.orglett.7b02471

DO - 10.1021/acs.orglett.7b02471

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EP - 5200

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Bromoallylation of alkenes leading to 4-alkenyl bromides based on trapping of β-bromoalkyl radicals

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