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Issue 42, 2013
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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

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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

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Publication details

The article was received on 09 Aug 2013, accepted on 17 Sep 2013 and first published on 17 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41632A
Citation: Org. Biomol. Chem., 2013,11, 7301-7317
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    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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