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Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation
Science China Chemistry ( IF 10.4 ) Pub Date : 2019-10-09 , DOI: 10.1007/s11426-019-9595-0
Takahide Fukuyama , Takashi Kippo , Kanako Hamaoka , Ilhyong Ryu

A radical chain addition of allyl bromides 2 to alkenylcyclopropanes 1 resulted in [3+2] annulation to give 2-bromomethyl-alkenylcyclopentanes 3 in good yields (16 examples). In this reaction, two kinetically fast radical reactions, cyclopropylcarbinyl radical-ring-opening and 5-exo-radical cyclization, preceded the β-fragmentation of a bromine radical to make the formal cycloaddition possible.



中文翻译:

自由基自由基介导的[3 + 2]环化:在光辐射下烯基环丙烷与烯丙基溴的反应合成2-溴甲基取代的烯基环戊烷

烯丙基溴2在链烯基环丙烷1上的自由基链加成导致[3 + 2]环化,以高收率得到2-溴甲基-烯基环戊烷3(16个实例)。在该反应中,先进行了两个动力学上快速的自由基反应,即环丙基羰基自由基的开环和5-外自由基的环化反应,然后再进行溴自由基的β片段化反应,从而使正式的环加成反应成为可能。

更新日期:2019-10-09
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