Homo- and heterodehydrocoupling of phosphines mediated by alkali metal catalysts

Lipeng Wu, Vincent T. Annibale, Haijun Jiao, Adam Brookfield, David Collison, Ian Manners

Research output: Contribution to journalArticlepeer-review


Catalytic chemistry that involves the activation and transformation of main group substrates is relatively undeveloped and current examples are generally mediated by expensive transition metal species. Herein, we describe the use of inexpensive and readily available tBuOK as a catalyst for P–P and P–E (E = O, S, or N) bond formation. Catalytic quantities of tBuOK in the presence of imine, azobenzene hydrogen acceptors, or a stoichiometric amount of tBuOK with hydrazobenzene, allow efficient homodehydrocoupling of phosphines under mild conditions (e.g. 25 °C and < 5 min). Further studies demonstrate that the hydrogen acceptors play an intimate mechanistic role. We also show that our tBuOK catalysed methodology is general for the heterodehydrocoupling of phosphines with alcohols, thiols and amines to generate a range of potentially useful products containing P–O, P–S, or P–N bonds.

Original languageEnglish
Article number2786
JournalNature Communications
Issue number1
Early online date26 Jun 2019
Publication statusPublished - 2019


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