Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans

Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans

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-enyn...

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Veröffentlicht in:Journal of organic chemistry 2022-07, Vol.87 (14), p.9250-9258
Hauptverfasser: Liu, Jiupeng, Tang, Shuo, Wang, Shichong, Cao, Mengting, Zhao, Jingjing, Zhang, Puyu, Li, Pan
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container_end_page 9258
container_issue 14
container_start_page 9250
container_title Journal of organic chemistry
container_volume 87
creator Liu, Jiupeng
Tang, Shuo
Wang, Shichong
Cao, Mengting
Zhao, Jingjing
Zhang, Puyu
Li, Pan
description 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.
doi_str_mv 10.1021/acs.joc.2c00989
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title Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans
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