Issue 80, 2019

1,1-Phosphinoboration of diazomethanes

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.

Graphical abstract: 1,1-Phosphinoboration of diazomethanes

Supplementary files

Article information

Article type
Communication
Submitted
04 Sept. 2019
Accepted
15 Sept. 2019
First published
16 Sept. 2019

Chem. Commun., 2019,55, 12100-12103

1,1-Phosphinoboration of diazomethanes

A. Trofimova, J. H. W. LaFortune, Z. Qu, S. A. Westcott and D. W. Stephan, Chem. Commun., 2019, 55, 12100 DOI: 10.1039/C9CC06914C

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