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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.

Chudasama, V; Akhbar, AR; Bahou, KA; Fitzmaurice, RJ; Caddick, S; (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. Org Biomol Chem , 11 (42) pp. 7301-7317. 10.1039/c3ob41632a. Green open access

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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.

Type: Article
Title: 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.
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c3ob41632a
Publisher version: http://dx.doi.org/10.1039/c3ob41632a
Additional information: © The Royal Society of Chemistry 2013. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1412929
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