Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation

被引：14

作者：

Fukuyama, Takahide ^{[1
]}

Kippo, Takashi ^{[1
]}

Hamaoka, Kanako ^{[1
]}

Ryu, Ilhyong ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Sakai, Osaka 5998531, Japan

来源：

SCIENCE CHINA-CHEMISTRY | 2019年 / 62卷 / 11期

基金：

日本学术振兴会;

关键词：

3+2] annulation; bromine radical; alkenylcyclopropanes; alkenylcyclopentanes; photo irradiation; RATE CONSTANTS; THIYL RADICALS; BROMOALLYLATION; ALKENES; CYCLOPROPYLCARBINYL; VINYLCYCLOPROPANES; FUNCTIONALIZATION; ADDITIONS; ALLENES; ALKYNES;

D O I：

10.1007/s11426-019-9595-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 beta-fragmentation of a bromine radical to make the formal cycloaddition possible.

引用

页码：1525 / 1528

页数：4

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