Tetrakis(dimethylamino)ethylene is a homogenous stoichiometric reductant, that exhibits high functional group tolerance.
The combination of a Ni catalyst with TDAE as sacrificial reductant enables a dicarbofunctionalization of a broad range of olefins with two electrophilic carbon sources under reductive conditions via simultaneous formation of one C(sp3)-C(sp3) and one C(sp3)-C(sp2) bond with exquisite selectivity.
W. Shu, A. García-Domínguez, M. T. Quirós, R. Mondal, D. J. Cárdenas, C. Nevado, J. Am. Chem. Soc., 2019, 141, 13812-13821.
An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with excellent enantioselectivity.
N. Suzuki, J. L. Hofstra, K. E. Poremba, S. E. Reisman, Org. Lett., 2017, 19, 2150-2153.