4.8 Review

Secondary phosphine oxides: Versatile ligands in transition metal-catalyzed cross-coupling reactions

Journal

COORDINATION CHEMISTRY REVIEWS
Volume 256, Issue 9-10, Pages 771-803

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.ccr.2011.11.007

Keywords

Secondary phosphine oxide (SPO); Cross-coupling; SPO in asymmetric reactions; Density functional theory (DFT); Palladium

Funding

  1. National Science Council of the ROC [NSC 95-2113-M-005-015-MY3]

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This review describes the development in the use of secondary phosphine oxides ligands in transition-metal-catalyzed oxidative coupling reactions to the formation of C-C, C-N and C-S bonds. Also the developments in the recent literature are highlighted in the areas of cycloaddition, coupling of acyl halide with organometallic reagents, oxidations and other reactions. The secondary phosphine oxides are known to exist in the tautomeric forms and are configurationally stable; this property enables a variety of useful transformations for accessing optically active organophosphorus compounds which are useful in the formation of C-C bonds and asymmetric hydrogenation reactions. Finally, the mechanistic aspect employing DFT technique in these oxidative coupling reactions is described in this article. (C) 2011 Elsevier B.V. All rights reserved.

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