Synthesis of 3-acylindoles by visible-light induced intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines.

Synthesis of 3-acylindoles by visible-light induced intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines.
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DOI:
10.1021/ol501276j
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发表时间:
2014-06
期刊:
影响因子:
5.2
通讯作者:
Ping Zhang;Tiebo Xiao;Sheng-Li Xiong;Xichang Dong;Lei Zhou
Ping Zhang;Tiebo Xiao;Sheng-Li Xiong;Xichang Dong;Lei Zhou
中科院分区:
化学1区
文献类型:
--
作者:
Ping Zhang;Tiebo Xiao;Sheng-Li Xiong;Xichang Dong;Lei Zhou

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本文报道了一种可见光光催化氧化还原合成3-酰基吲哚的新方法。该反应在温和的反应条件下使用空气作为氧化剂有效地进行,并且仅生成水作为副产物。提出了一种可能的反应机理,包括α-氨基烷基与炔加成,然后形成C-O键。
A visible-light photoredox synthesis of 3-acylindoles through intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines is developed. The reaction proceeds effectively under mild reaction conditions using air as the oxidant, and only water is generated as a side product. A plausible mechanism involving the addition of α-amino alkyl radicals to alkynes, followed by C-O bond formation, is proposed.