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.
A highly efficient asymmetric intermolecular Ni-catalyzed reductive dicarbofunctionalization of vinyl amides, vinyl boranes, or vinyl phosphonates with two distinct readily available electrophiles, namely, Csp2- and Csp3-halides, provides chiral products in a highly regio- and enantioselective manner.
X. Wei, W. Shu, A. García-Domínguez, E. Merino, C. Nevado, J. Am. Chem. Soc., 2020, 142, 13515-13522.
A photoinduced reduction of trifluoromethyl iodide by tetrakis(dimethylamino)ethylene (TDAE) enables a nucleophilic trifluoromethylation of aldehydes and ketones.
S. Aït-Mohand, N. Takechi, M. Médebielle, W. R. Dolbier, Org. Lett., 2001, 3, 4271-4273.
An asymmetric homocoupling of ortho-(iodo)arylphosphine oxides and ortho-(iodo)arylphosphonates provides highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates without need for optical resolution. These products are readily converted to biaryl bisphosphines. The conditions have also proven effective for asymmetric dimerization of non-phosphorus-containing aryl halides.
Z. Zuo, R. S. Kim, D. A. Watson, J. Am. Chem. Soc., 2021, 143, 1328-1333.