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Cu(I)-Catalyzed ortho-Selective Cross-Coupling of Phenols with Electrophilic Indoles

Title
Cu(I)-Catalyzed ortho-Selective Cross-Coupling of Phenols with Electrophilic Indoles
Other Titles
Cu(I)-촉매에 의한 친전자성 인돌과 페놀의 위치선택적 짝지움반응
Author
오수민
Alternative Author(s)
오수민
Advisor(s)
신숭훈
Issue Date
2021. 2
Publisher
한양대학교
Degree
Master
Abstract
Direct functionalization of inert C-H bonds is an attractive strategy and therefore have drawn intense interest. To implement such a strategy for regioselective functionalization of phenols, we introduced herein N-(acyloxy)indole as electrophilic, umpoled indole derivatives. In this presentation, we developed a new protocol for a general synthesis of N-(acyloxy)indoles, based on the electrophilic cyclization of (o-alkynyl)phenylhydroxylamines. With an easy access to a variety of N-(acyloxy)indoles, we developed a Cu(I) catalyzed ortho-selective coupling of phenols with the umpoled indoles. The [Cu(OTf)]2·C6H6 system was extremely reactive and catalyzed the coupling at a very low loading (0.1 - 0.01 mol%) and at room temperature. The unusual C2-regioselectivity was rationalized by a sequence comprising N-substitution, followed by [3,3]-sigmatropic rearrangement.
URI
https://repository.hanyang.ac.kr/handle/20.500.11754/159005http://hanyang.dcollection.net/common/orgView/200000485419
Appears in Collections:
GRADUATE SCHOOL[S](대학원) > CHEMISTRY(화학과) > Theses (Master)
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