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Issue 13, 2019
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Dithiane-directed Rh(iii)-catalyzed amidation of unactivated C(sp3)–H bonds

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Abstract

An oxidant-free Rh(III)-catalyzed direct amidation of alkyl dithianes via C(sp3)–H bond activation utilizing diverse and robust dioxazolone reagents is reported. The reaction hinges on use of a Cp*Rh(III) complex in combination with an essential amino-carboxylate additive to generate usefully protected 1,3-aminoaldehyde derivatives. The scalability of the reaction was demonstrated as was a series of downstream product functionalizations, including dithiane deprotection, anion alkylation and reductive desulfurization, highlighting the general applicability of this transformation in the synthesis of novel scaffolds and building blocks.

Graphical abstract: Dithiane-directed Rh(iii)-catalyzed amidation of unactivated C(sp3)–H bonds

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Supplementary files

Article information


Submitted
23 Nov 2018
Accepted
18 Feb 2019
First published
18 Feb 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 3733-3737
Article type
Edge Article

Dithiane-directed Rh(III)-catalyzed amidation of unactivated C(sp3)–H bonds

H. Shi and D. J. Dixon, Chem. Sci., 2019, 10, 3733
DOI: 10.1039/C8SC05225E

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