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Metal‐Catalyzed Regiospecific (4+3) Cyclization of 2‐Indolylmethanols with ortho ‐Quinone Methides
Author(s) -
Zhou SiJia,
Sun Meng,
Wang JingYi,
Yu XianYang,
Lu Han,
Zhang YuChen,
Shi Feng
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000693
Subject(s) - chemistry , nucleophile , regioselectivity , indole test , quinone , catalysis , metal , combinatorial chemistry , organic chemistry , medicinal chemistry
The first metal‐catalyzed C3‐nucleophilic (4+3) cyclization of 2‐indolylmethanols with stable ortho ‐quinone methides has been established, which constructed indole‐based seven‐membered heterocycles in high yields (70 %‐98 %) with regiospecificity. This reaction has tackled the challenges in exploring the C3‐nucleophilicity of 2‐indolylmethanols, which will contribute to the chemistry of 2‐indolylmethanols, especially to metal‐catalyzed cyclizations of 2‐indolylmethanols. In addition, this approach will provide a useful method for constructing indole‐based seven‐membered heterocycles with high efficiency and regioselectivity.