Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 28, Pages 4301-4308Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000693
Keywords
Cyclization; 2-Indolylmethanol; ortho-Quinone methide; Homogeneous catalysis; Indole
Categories
Funding
- NSFC [21772069, 21831007]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
- TAPP
- Undergraduate Students Project of JSNU
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The first metal-catalyzed C3-nucleophilic (4+3) cyclization of 2-indolylmethanols with stableortho-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.
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