Metal‐Catalyzed Regiospecific (4+3) Cyclization of 2‐Indolylmethanols with ortho‐Quinone Methides

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 explorin...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-08, Vol.2020 (28), p.4301-4308
Main Authors: Zhou, Si‐Jia, Sun, Meng, Wang, Jing‐Yi, Yu, Xian‐Yang, Lu, Han, Zhang, Yu‐Chen, Shi, Feng
Format: Article
Language:English
Subjects:
2‐Indolylmethanol
Cyclization
Homogeneous catalysis
Indole
ortho‐Quinone methide
Quinones
Regioselectivity
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Summary: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. The first metal‐catalyzed C3‐nucleophilic (4+3) cyclization of 2‐indolylmethanols with stable ortho‐quinone methides has been established, which was used to construct indole‐based seven‐membered heterocycles in high yields (up to 98 %) with regiospecificity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000693