Premium
Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C−H Aminations
Author(s) -
Tian Xianhai,
Song Lina,
Hashmi A. Stephen K.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202000146
Subject(s) - nitrene , amination , intramolecular force , chemistry , combinatorial chemistry , yield (engineering) , aryl , catalysis , organic synthesis , photochemistry , organic chemistry , materials science , alkyl , metallurgy
While direct nitrene insertions into C−H bonds have become an important tool for building C−N bonds in modern organic chemistry, the generation of nitrene intermediates always requires transition metals, high temperatures, ultraviolet or laser light. We report a mild synthesis of carbazoles and related building blocks through a visible light‐induced intramolecular C−H amination reaction. A striking advantage of this new method is the use of more reactive aryl sulfilimines instead of the corresponding hazardous azides. Different catalysts and divergent light sources were tested. The reaction scope is broad and the product yield is generally high. An efficient gram‐scale synthesis of Clausine C demonstrates the applicability and scalability of this new method.