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Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions

Title
Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions
Author
윤소원
Keywords
carbazoles; C-H activation; palladium catalysis; regioselectivity
Issue Date
2019-02
Publisher
WILEY-V C H VERLAG GMBH
Citation
ADVANCED SYNTHESIS & CATALYSIS, v. 361, NO 3, Page. 462-468
Abstract
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.
URI
https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201801265http://repository.hanyang.ac.kr/handle/20.500.11754/108475
ISSN
1615-4150; 1615-4169
DOI
10.1002/adsc.201801265
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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