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Bromoallylation of Alkenes Leading to 4-Alkenyl Bromides Based on Trapping of β-Bromoalkyl Radicals
- Kippo, Takashi, Hamaoka, Kanako, Ueda, Mitsuhiro, Fukuyama, Takahide, Ryu, Ilhyong
- Organic letters 2017 v.19 no.19 pp. 5198-5200
- alkenes, bromides, chemical structure, cyclization reactions, cyclohexanones, free radicals, organobromine compounds, phthalimide, piperidines, trapping
- 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.