Molecules 2012, 17(12), 14573-14587; doi:10.3390/molecules171214573
Review

Stoichiometric and Catalytic Synthesis of Alkynylphosphines

Elise Bernoudemail, Romain Veillardemail, Carole Alayrac* email and Annie-Claude Gaumont* email
Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 14050 Caen, France
* Authors to whom correspondence should be addressed.
Received: 23 November 2012; in revised form: 29 November 2012 / Accepted: 5 December 2012 / Published: 7 December 2012
(This article belongs to the Special Issue Organophosphorus Chemistry)
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Abstract: Alkynylphosphines or their borane complexes are available either through C–P bond forming reactions or through modification of the phosphorus or the alkynyl function of various alkynyl phosphorus derivatives. The latter strategy, and in particular the one involving phosphoryl reduction by alanes or silanes, is the method of choice for preparing primary and secondary alkynylphosphines, while the former strategy is usually employed for the synthesis of tertiary alkynylphosphines or their borane complexes. The classical C–P bond forming methods rely on the reaction between halophosphines or their borane complexes with terminal acetylenes in the presence of a stoichiometric amount of organometallic bases, which precludes the access to alkynylphosphines bearing sensitive functional groups. In less than a decade, efficient catalytic procedures, mostly involving copper complexes and either an electrophilic or a nucleophilic phosphorus reagent, have emerged. By proceeding under mild conditions, these new methods have allowed a significant broadening of the substituent scope and structure complexity.
Keywords: organophosphorus chemistry; phosphines; phosphine-boranes; homogeneous catalysis

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MDPI and ACS Style

Bernoud, E.; Veillard, R.; Alayrac, C.; Gaumont, A.-C. Stoichiometric and Catalytic Synthesis of Alkynylphosphines. Molecules 2012, 17, 14573-14587.

AMA Style

Bernoud E, Veillard R, Alayrac C, Gaumont A-C. Stoichiometric and Catalytic Synthesis of Alkynylphosphines. Molecules. 2012; 17(12):14573-14587.

Chicago/Turabian Style

Bernoud, Elise; Veillard, Romain; Alayrac, Carole; Gaumont, Annie-Claude. 2012. "Stoichiometric and Catalytic Synthesis of Alkynylphosphines." Molecules 17, no. 12: 14573-14587.

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