Issue 14, 2007

Bis(diphenylphosphino)acetonitrile: Synthesis, ligand properties and application in catalytic carbon–carbon coupling

Abstract

Treatment of acetonitrile (1 equiv.) with n-butyllithium (0.95 equiv.) followed by chlorodiphenylphosphine (0.95 equiv.) under optimised reaction conditions gave a ca. 60% yield of bis(diphenylphosphino)acetonitrile (dppmCN, 1). The bidentate ligand was employed in the synthesis of the four-membered chelate metal complexes (dppmCN)MCl2 [M = Pd (6a), Pt (6b)] and (dppmCN)RuCp*(Cl) (7). A very active catalyst for bromobenzene/phenylboronic acid Suzuki–Miyaura coupling was in situ generated by treatment of Pd(OAc)2 with bis(diphenylphosphino)acetonitrile [TOF (1 h) >600000].

Graphical abstract: Bis(diphenylphosphino)acetonitrile: Synthesis, ligand properties and application in catalytic carbon–carbon coupling

Supplementary files

Article information

Article type
Paper
Submitted
17 Nov 2006
Accepted
29 Jan 2007
First published
20 Feb 2007

Dalton Trans., 2007, 1409-1415

Bis(diphenylphosphino)acetonitrile: Synthesis, ligand properties and application in catalytic carbon–carbon coupling

L. Braun, P. Liptau, G. Kehr, J. Ugolotti, R. Fröhlich and G. Erker, Dalton Trans., 2007, 1409 DOI: 10.1039/B616847G

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