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Chudasama V, Akhbar AR, Bahou KA, et al. Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof. Org Biomol Chem. 2013;11(42):7301-17doi: 10.1039/c3ob41632a.
Chudasama, V., Akhbar, A. R., Bahou, K. A., Fitzmaurice, R. J., & Caddick, S. (2013). Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof. Organic & biomolecular chemistry, 11(42), 7301-17. https://doi.org/10.1039/c3ob41632a
Chudasama, Vijay, et al. "Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof." Organic & biomolecular chemistry vol. 11,42 (2013): 7301-17. doi: https://doi.org/10.1039/c3ob41632a
Chudasama V, Akhbar AR, Bahou KA, Fitzmaurice RJ, Caddick S. Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof. Org Biomol Chem. 2013 Nov 14;11(42):7301-17. doi: 10.1039/c3ob41632a. PMID: 24068290.
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Org Biomol Chem. 2013 Nov 14;11(42):7301-17. doi: 10.1039/c3ob41632a.

Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof.

Organic & biomolecular chemistry

Vijay Chudasama, Ahmed R Akhbar, Karim A Bahou, Richard J Fitzmaurice, Stephen Caddick

Affiliations

  1. Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK. [email protected].

PMID: 24068290 DOI: 10.1039/c3ob41632a

Abstract

In this report, a thorough evaluation of the use of aerobically initiated, metal-free hydroacylation of various C=C and N=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.

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