Secondary phosphines are compounds of great potential utility. Synthesis of secondary phosphines typically relies on reaction of organometallic reagents with halophosphines, hyrdrophosphination reactions, or chemical reduction of secondary phosphine derivatives. These methodologies limit the variety of secondary phosphines easily accessible to reasearchers. One potentially powerful synthetic tool for the synthesis of secondary phosphines is P–C cross-coupling. Pd-catalyzed P–C cross-coupling reactions have been used in the synthesis of a variety of tertiary phosphines, with special focus placed on the generation of chiral at phosphorus products. Contrastingly, there are few reports of the application of cross-coupling methodologies to the synthesis of secondary phosphines. Here we report the development of a copper-catalyzed P–C cross-coupling reaction that provides selective access to a variety of asymmetric secondary phophines in high conversions and short reactions times. The method also allows facile access to secondary phosphine ligands that are traditionally laborious or difficult to synthesize, such as 1,8-bis(arylphosphino)naphthalenes.

Copper-catalyzed P–C cross-coupling for the synthesis of secondary phosphines and related ligands.

255th National Meeting (2018)

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