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Palladium‐Catalyzed Regioselective Synthesis of 1‐Hydroxycarbazoles Under Aerobic Conditions
Author(s) -
Youn So Won,
Kim Young Ho,
Jo Yoon Hyung
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801265
Subject(s) - regioselectivity , chemistry , palladium , carbazole , steric effects , catalysis , combinatorial chemistry , organic chemistry
A palladium‐catalyzed aerobic C−H amidation of N ‐Ts‐2‐amino‐3′‐hydroxylbiaryls has been developed to afford a diverse range of 1‐hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, and sustainability with the use of ambient air as the sole terminal oxidant. Further elaboration of the products obtained from this process provides facile access to various carbazole alkaloids including carbazolequinones and biscarbazoles. A mechanism involving dual directing group‐assisted regioselective C−H activation at the more sterically hindered C2′‐position of 2‐amino‐3′‐hydroxylbiaryls is proposed.