Categories: C-P Bond Formation >

Synthesis of phosphines

Recent Literature

A versatile and efficient Pd(OAc)₂/1,1'-bis(diisopropylphosphino)ferrocene-catalyzed cross-coupling of thiols with aryl halides was developed. Aryl bromides and chlorides can be coupled to aliphatic and aromatic thiols - the widest substrate scope of any reported to date. This catalyst system also enables the coupling of secondary phosphines with aryl halides.
M. Murata, S. L. Buchwald, Tetrahedron, 2004, 60, 7397-7403.

A series of novel functionalized, hemilabile phosphines have been prepared from diaryl­phosphines using several synthetic methodologies - including  alkylation of lithium diarylphosphide or (di­arylphosphino)borane adducts with functionalized halogenoalkanes and the photochemical hydrophosphination of suitable functionalized allyl or vinyl derivatives using white light.
M. V. Jiménez, J. J. Pérez-Torrente, M. I. Bartolomé, L. A. Oro, Synthesis, 2009, 1916-1922.

Triazole-based monophosphine ligands have been prepared via efficient cycloadditions. Palladium complexes derived from these ligands are highly active catalysts for Suzuki-Miyaura coupling and amination reactions of aryl chlorides.
D. Liu, W. Gao, Q. Dai, X. Zhang, Org. Lett., 2005, 7, 4907-4910.

A [Cu(OH)•TMEDA]₂Cl₂ catalyzed tandem reaction allows the synthesis of a series of sterically and electronically divergent phenacyl tertiary phosphine-boranes.
G. Kumaraswamy, G. V. Rao, A. N. Murthy, B. Sridhar, Synlett, 2009, 1180-1184.

Related A stereoselective hydrophosphination reaction of alkynes with diphenylphosphane has been developed. The reaction is mediated by a cobalt catalyst and butyllithium. H. Ohmiya, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed., 2005, 44, 2368-2370. Several E and Z configured α,β-unsaturated carbonyl and carboxyl acceptors (including imides) as well as nitroalkenes participate in a palladium(II)-catalyzed conjugate transfer of diphenyl-, dicyclohexyl-, and di-tert-butylphosphinyl groups from silylphosphines in high chemical yields. V. T. Trepohl, S. Mori, K. Itami, M. Oestreich, Org. Lett., 2009, 11, 1091-1094.