期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 29, 页码 9856-9860出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201904709
关键词
alkynes; C-H activation; heterocycles; iridium; sulfur
资金
- JSPS KAKENHI [JP 17H06092]
Indoles and their analogues have been one of the most ubiquitous heterocycles during the past century, and extensive studies have been conducted to establish practical synthetic methods for their derivatives. In particular, selective functionalization of the poorly reactive benzenoid core over the pyrrole ring has been a great challenge. Reported herein is an iridium-catalyzed direct alkynylation of the indole C4- and C7-positions with the assistance of sulfur directing groups. This transformation shows a wide range of functional-group tolerance with exceptional site selectivity. The directing group can be either easily removed or transformed after catalysis. The synthetic utility of the alkyne fragment is demonstrated by the derivatization into the core structure of natural indole alkaloids.
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