Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof.
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.
Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK. VPEnterprise@ucl.ac.uk.
Vijay
V
Chudasama
Ahmed R
AR
Akhbar
Karim A
KA
Bahou
Richard J
RJ
Fitzmaurice
Stephen
S
Caddick