N-Heterocyclic Carbene-Stabilized Germanium and Tin Analogues of Heavier Nitriles: Synthesis, Reactivity, and Catalytic Application.

Author(s) Nesterov, V.; Baierl, R.; Hanusch, F.; Ferao, A.Espinosa; Inoue, S.
Journal J Am Chem Soc
Date Published 2019 Sep 18
Abstract

The synthesis of stable heavier analogues of nitriles as monomeric tetrylene-phosphinidenes TerEP(IDipp) (E = Ge, Sn; Ter = 2,6-MesCH, IDipp = C([N-(2,6-PrCH)CH]) was achieved by taking advantage of NHC (N-heterocyclic carbene, here IDipp) coordination to the low-valent phosphorus center. Multiple bonding character of the E-P bonds was examined experimentally and computationally. Both germanium and tin compounds undergo [2+2] cycloaddition with diphenylketene, whereas reaction of the tin derivative with (pentafluorophenyl)borane provided unique "push-pull" phosphastannene (Ter)(Ar)Sn = P(IDipp) (Ar = CF[B(F)(CF)]). Going further, we demonstrated the potential of tetrylene-phosphinidene complexes in catalytic hydroboration of carbonyl compounds.

DOI 10.1021/jacs.9b08741
ISSN 1520-5126
Citation Nesterov V, Baierl R, Hanusch F, Ferao AE, Inoue S. N-Heterocyclic Carbene-Stabilized Germanium and Tin Analogues of Heavier Nitriles: Synthesis, Reactivity, and Catalytic Application. J Am Chem Soc. 2019;141(37):14576-14580.