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Updated: Apr 28, 2026
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Oxidative addition of σ bonds to an Al(I) center
Terry Chu1, Ilia Korobkov, Georgii I Nikonov
1Department of Chemistry, Brock University , 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada.
Abstract:
The Al(I) compound NacNacAl (1, NacNac = [ArNC(Me)CHC(Me)NAr](-) and Ar = 2,6-Pr(i)2C6H3) reacts with H-X (X = H, Si, B, Al, C, N, P, O) σ bonds of H2, silanes, borane (HBpin, pin = pinacolate), allane (NacNacAlH2), phosphine (HPPh2), amines, alcohol (Pr(i)OH), and Cp*H (Cp* = pentamethylcyclopentadiene) to give a series of hydride derivatives of the four-coordinate aluminum NacNacAlH(X), which are characterized herein by spectroscopic methods (NMR and IR) and X-ray diffraction. This method allows for the syntheses of the first boryl hydride of aluminum and novel silyl hydride and phosphido hydride derivatives. In the case of the addition of NacNacAlH2, the reaction is reversible, proving the possibility of reductive elimination from the species NacNacAlH(X).
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