Reductive Elimination at Carbon under Steric Control

D. R. Tolentino, S. E. Neale, C. J. Isaac, S. A. Macgregor, M. K. Whittlesey, R. Jazzar, G. Bertrand
JACS (Journal of the American Chemical Society)
141 (25), 9823-9826
Published while none of the authors were employed at the CMM


It has been previously demonstrated that stable singlet electrophilic carbenes can behave as metal surrogates in the activation of strong E–H bonds (E = H, B, N, Si, P), but it was believed that these activations only proceed through an irreversible activation barrier. Herein we show that, as is the case with transition metals, the steric environment can be used to promote reductive elimination at carbon centers.