Organic Letters
Organic Letters
5 years ago

Bromoallylation of Alkenes Leading to 4-Alkenyl Bromides Based on Trapping of β-Bromoalkyl Radicals

Bromoallylation of Alkenes Leading to 4-Alkenyl Bromides Based on Trapping of β-Bromoalkyl Radicals
Takahide Fukuyama, Ilhyong Ryu, Takashi Kippo, Mitsuhiro Ueda, Kanako Hamaoka
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02471

DOI: 10.1021/acs.orglett.7b02471

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