Tris(dimethylamino)phosphine, P(NMe2)3
Tris(dimethylamino)phosphine can be used as a deoxygenation and desulfurization agent.
Recent Literature
P(NMe2)3 mediates umpolung alkylation
of methyl aroylformates with benzylic and allylic bromides via a two-electron redox addition of the
tricoordinate phosphorus reagent to the α-keto ester compound (Kukhtin-Ramirez
addition). Depending on the work-up conditions, either
Barbier-type addition or ylide-free olefination products can be isolated.
S. R. Wang, A. T. Radosevich, Org. Lett.,
2015,
17, 3810-3813.
Adducts derived from P(NMe2)3 and α-ketoesters are
effectively intercepted by N-sulfonyl imines, affording a range of
aziridine-2-carboxylates. The diastereoselectivity of this aziridination depends
on steric hindrance from substituents on the substrates.
J. Jiang, H. Liu, C.-D. Lu, Y.-J. Xu, J. Org. Chem.,
2017, 82, 811-818.
A P(NMe2)3-mediated tandem (1 + 4) annulation
between aroylformates and δ-tosylamino enones provides functionalized
pyrrolidines in good yields with exclusive chemoselectivity and high
diastereoselectivity. The reaction proceeds through an unprecedented P(NMe2)3-mediated
reductive amination/base-catalyzed Michael addition cascade.
R. Liu, J. Liu, J. Cao, R. Li, R. Zhou, Y. Qiao, W.-C. Gao,
Org. Lett., 2020, 22, 6922-6926.
A simple P(NMe2)3-mediated annulation reaction of N-acyldiazenes
with isothiocyanates provides 2-imino-1,3,4-thiadiazoles. N-acyldiazenes
can be generated from hydrazides using iodine as oxidant and can be used without
purification.
Z. Huang, Q. Zhang, Q. Zhao, W. Yu, J. Chang,
Org. Lett., 2020, 22, 4378-4382.
