Issue 42, 2013

Metal-free, hydroacylation of C[double bond, length as m-dash]C and N[double bond, length as m-dash]N bonds via aerobic C–H activation of aldehydes, and reaction of the products thereof

Abstract

In this report, a thorough evaluation of the use of aerobically initiated, metal-free hydroacylation of various C[double bond, length as m-dash]C and N[double bond, length as m-dash]N acceptor molecules with a wide range of aldehydes is presented. The aerobic-activation conditions that have been developed are in sharp contrast to previous conditions for hydroacylation, which tend to use transition metals, peroxides that require thermal or photochemical degradation, or N-heterocyclic carbenes. The mildness of the conditions enables a number of reactions involving sensitive reaction partners and, perhaps most significantly, allows for α-functionalised chiral aldehydes to undergo radical-based hydroacylation with complete retention of optical purity. We also demonstrate how the resulting hydroacylation products can be transformed into other useful intermediates, such as γ-keto-sulfonamides, sultams, sultones, cyclic N-sulfonyl imines and amides.

Graphical abstract: Metal-free, hydroacylation of C [[double bond, length as m-dash]] C and N [[double bond, length as m-dash]] N bonds via aerobic C–H activation of aldehydes, and reaction of the products thereof

Supplementary files

Article information

Article type
Paper
Submitted
09 Aug 2013
Accepted
17 Sep 2013
First published
17 Sep 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2013,11, 7301-7317

Metal-free, hydroacylation of C[double bond, length as m-dash]C and N[double bond, length as m-dash]N bonds via aerobic C–H activation of aldehydes, and reaction of the products thereof

V. Chudasama, A. R. Akhbar, K. A. Bahou, R. J. Fitzmaurice and S. Caddick, Org. Biomol. Chem., 2013, 11, 7301 DOI: 10.1039/C3OB41632A

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