Jump to main content
Jump to site search

Issue 26, 2007
Previous Article Next Article

Synthesis, coordination and catalytic use of 1-(diphenylphosphino)-1′-carbamoylferrocenes with pyridyl-containing N-substituents

Author affiliations

Abstract

Ferrocene phosphinocarboxamides, 1-(diphenylphosphino)-1′-{N-[(2-pyridyl)methyl]carbamoyl}ferrocene (1) and 1-(diphenylphosphino)-1′-{N-[2-(2-pyridyl)ethyl]carbamoyl}ferrocene (2) were prepared from 1-(diphenylphosphino)-1′-ferrocenecarboxylic acid and studied as ligands for palladium. Starting with [PdCl2(cod)], the reactions at a 2 : 1 ligand-to-metal ratio gave uniformly the bis-phosphine complexes [PdCl2(L-κP)2] (3, L = 1; 4, L = 2) whereas those performed at a 1 : 1 ratio yielded distinct products: [PdCl2(12P,N)] (5) with 1 coordinating as a trans-spanning P,N-donor, and the symmetric, P,N-bridged dimer [(µ-2-N,P)2{PdCl2}2] (6), respectively. The crystal structures of 1, 2, 4·4CHCl3, 5·AcOH, and 6·8CHCl3 as determined by X-ray diffraction showed the compounds to form well defined solid-state assemblies through hydrogen bonds. Testing of the phosphinocarboxamides in the palladium-catalysed Suzuki cross-coupling reaction revealed 1 and 2, combined with Pd(OAc)2 to form efficient catalysts for the reactions of aryl bromides while aryl chlorides coupled only when activated with electron-withdrawing groups.

Graphical abstract: Synthesis, coordination and catalytic use of 1-(diphenylphosphino)-1′-carbamoylferrocenes with pyridyl-containing N-substituents

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Jan 2007, accepted on 17 Apr 2007 and first published on 04 May 2007


Article type: Paper
DOI: 10.1039/B701012E
Citation: Dalton Trans., 2007,0, 2802-2811
  •   Request permissions

    Synthesis, coordination and catalytic use of 1-(diphenylphosphino)-1′-carbamoylferrocenes with pyridyl-containing N-substituents

    J. Kühnert, M. Dušek, J. Demel, H. Lang and P. Štěpnička, Dalton Trans., 2007, 0, 2802
    DOI: 10.1039/B701012E

Search articles by author

Spotlight

Advertisements