標題: | Bromoallylation of Alkenes Leading to 4-Alkenyl Bromides Based on Trapping of beta-Bromoalkyl Radicals |
作者: | Kippo, Takashi Hamaoka, Kanako Ueda, Mitsuhiro Fukuyama, Takahide Ryu, Ilhyong 應用化學系 Department of Applied Chemistry |
公開日期: | 6-Oct-2017 |
摘要: | A radical-chain addition of allyl bromides to aryl alkenes, vinyl ester, and vinyl phthalimide was studied in which elusive beta-bromodkyl 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. |
URI: | http://dx.doi.org/10.1021/acs.orglett.7b02471 http://hdl.handle.net/11536/143913 |
ISSN: | 1523-7060 |
DOI: | 10.1021/acs.orglett.7b02471 |
期刊: | ORGANIC LETTERS |
Volume: | 19 |
起始頁: | 5198 |
結束頁: | 5200 |
Appears in Collections: | Articles |