Brønsted Base Mediated Stereoselective Diphosphination of Terminal Alkynes with Diphosphanes

Organic Letters
Yuto OkugawaMasahiro Miura

Abstract

A Brønsted base mediated stereoselective diphosphination of terminal alkynes with diphosphanes proceeds to deliver the corresponding (E)-1,2-diphosphinoethenes in good yields. The reaction of aromatic alkynes occurs efficiently in the presence of a catalytic amount of LiO-t-Bu while MN(TMS)2 (M = Li or Na) gave better results in the case of aliphatic substrates. The Brønsted base mediated protocol can offer a good alternative to precedented transition-metal-catalyzed or radical-promoted approaches to the 1,2-diphosphinoethene framework of potent interest in catalysis and coordination chemistry.

References

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May 5, 2010·Journal of the American Chemical Society·Zhong-Ming SunPinjing Zhao
Nov 13, 2013·Journal of the American Chemical Society·Sobi AsakoEiichi Nakamura
Dec 10, 2015·Journal of the American Chemical Society·Rajagopal SanthoshkumarChien-Hong Cheng
Apr 18, 2017·Journal of the American Chemical Society·Yuto UnohMasahiro Miura

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