Iridium‐Catalyzed Direct C4‐ and C7‐Selective Alkynylation of Indoles Using Sulfur‐Directing Groups
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 p...
Saved in:
Published in | Angewandte Chemie International Edition Vol. 58; no. 29; pp. 9856 - 9860 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
15.07.2019
Wiley Subscription Services, Inc |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | 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.
S‐directed: An iridium‐catalyzed direct alkynylation for the indole C4‐ and C7‐positions was achieved with the assistance of sulfur directing groups. The transformation shows broad functional‐group tolerance with complete site selectivity, and the directing group can be either easily removed or transformed after the reaction. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.201904709 |