Tetrakis(dimethylamino)ethylene, TDAE
Tetrakis(dimethylamino)ethylene is a homogenous stoichiometric reductant, that exhibits high functional group tolerance.
Recent Literature
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.
