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Updated: Jan 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
1,1-Phosphinoboration of diazomethanes
Alina Trofimova1, James H W LaFortune1, Zheng-Wang Qu2
1Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada. douglas.stephan@utoronto.ca.
Abstract:
The reactions of the phosphinoboranes Ph2PBMes2, Ph2PBpin, and Ph2PBcat with the diazomethanes Ph2CN2, C12H8CN2, and EtO2CCHN2 are shown to give products of 1,1-phosphinoboration. The products (1-6) are shown to have PNB linkages with three-coordinate boron centers, whereas the products (EtOOC)CNN(PR2)(Bpin) (R = Ph 7, tBu 8) form zwitterionic heterocycles resulting from chelation of the ester carbonyl to boron. DFT calculations show that the reactions are initiated by N-to-B addition followed by 1,2-phosphinyl shift.
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