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Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2022-06-24 , DOI: 10.1021/acs.joc.2c00989
Jiupeng Liu 1 , Shuo Tang 1 , Shichong Wang 1 , Mengting Cao 1 , Jingjing Zhao 1 , Puyu Zhang 1 , Pan Li 1
Affiliation  

Visible-light-induced 1,6-enyne-triggered C–Br bond homolysis of bromomalonates has been developed. This transition-metal-free, photocatalyst-free, and oxidant- and additive-free protocol affords an efficient approach for divergent synthesis of carbonylated and hydroxylated benzofurans from 1,6-enynes and bromomalonates under mild conditions. Significantly, mechanistic studies reveal that the homolysis of C–Br bonds appears to experience an energy-transfer pathway, and the atom-transfer radical addition products are the key intermediates to generate carbonylated and hydroxylated benzofurans.

中文翻译:

可见光诱导的 1,6-烯炔引发溴丙二酸酯的 C-Br 键均解:羰基化和羟基化苯并呋喃的溶剂控制发散合成

已经开发了溴丙二酸的可见光诱导的 1,6-烯炔触发的 C-Br 键均裂。这种无过渡金属、无光催化剂、无氧化剂和无添加剂的方案为在温和条件下从 1,6-烯炔和溴丙二酸进行不同合成羰基化和羟基化苯并呋喃提供了一种有效的方法。重要的是,机理研究表明,C-Br 键的均裂似乎经历了能量转移途径,原子转移自由基加成产物是生成羰基化和羟基化苯并呋喃的关键中间体。
更新日期:2022-06-24
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