Tris(dimethylamino)phosphine can be used as a deoxygenation and desulfurization agent.
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.