Issue 13, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2019,10, 3733-3737

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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