Room-temperature palladium-catalyzed Negishi-type coupling: a combined experimental and theoretical study

Philippe Ribagnac; Matthias Blug; Jose Villa-Uribe; Xavier-Frédéric Le Goff; Corinne Gosmini; Nicolas Mézailles

doi:10.1002/chem.201102369

Room-temperature palladium-catalyzed Negishi-type coupling: a combined experimental and theoretical study

Chemistry. 2011 Dec 16;17(51):14389-93. doi: 10.1002/chem.201102369. Epub 2011 Nov 25.

Authors

Philippe Ribagnac¹, Matthias Blug, Jose Villa-Uribe, Xavier-Frédéric Le Goff, Corinne Gosmini, Nicolas Mézailles

Affiliation

¹ Laboratoire Hétéroéléments et Coordination, Ecole Polytechnique, CNRS, 91128 Palaiseau Cedex, France.

PMID: 22120927
DOI: 10.1002/chem.201102369

Abstract

An air-stable, bulky electron-accepting phosphine ligand (phosphabarrelene) allows the easy reduction of a Pd(II) precursor to a Pd(0) complex, highly active in room-temperature Negishi-type cross-coupling. DFT calculations show that the use of the electron-accepting ligand favors both transmetalation (TM) and reductive-elimination (RE) processes (see scheme; OA = oxidative addition).