Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 39, Pages 5443-5448Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100964
Keywords
C-H activation; Halogenation; N-Halosuccinimides; Indolines; Rhodium catalyst
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An efficient Rh-catalyzed method has been developed for selective C7 halogenation of N-pyrimidyl indolines, producing corresponding halides in good to excellent yields. The strategy demonstrates broad substrate scope, excellent regioselectivity for C7 functionalization of indolines, and feasibility at gram scale level. Various control experiments were conducted to understand the reaction pathway, and the applicability of the methodology was demonstrated by synthesis of indoles and post-transformation of the C7 halogenated indolines into different valuable molecules.
An efficient Rh-catalyzed catalytic method has been developed for selective C7 halogenation of N-pyrimidyl indolines with N-halosuccinimides (Cl, Br, I) to produce corresponding halides in good to excellent yields. The advantages of this strategy include broad substrate scope and excellent regioselectivity for C7 functionalization of indolines and feasibility at gram scale level. Various control experiments have been performed to understand the reaction pathway. Applicability of current methodology has been demonstrated by indole synthesis and post-transformation of the C7 halogenated indolines into different valuable molecules.
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