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Tetramethylphosphinane as a new secondary phosphine synthon.

James D NobbsSigit SugiartoXin Yi SeeChoon Boon CheongSrinivasulu AitipamulaLudger P StubbsMartin van Meurs
Published in: Communications chemistry (2023)
Secondary phosphines are important building blocks in organic chemistry as their reactive P-H bond enables construction of more elaborate molecules. In particular, they can be used to construct tertiary phosphines that have widespread applications as organocatalysts, and as ligands in metal-complex catalysis. We report here a practical synthesis of the bulky secondary phosphine synthon 2,2,6,6-tetramethylphosphinane (TMPhos). Its nitrogen analogue tetramethylpiperidine, known for over a century, is used as a base in organic chemistry. We obtained TMPhos on a multigram scale from an inexpensive air-stable precursor, ammonium hypophosphite. TMPhos is also a close structural relative of di-tert-butylphosphine, a key component of many important catalysts. Herein we also describe the synthesis of key derivatives of TMPhos, with potential applications ranging from CO 2 conversion to cross-coupling and beyond. The availability of a new core phosphine building block opens up a diverse array of opportunities in catalysis.
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