Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 749, Issue -, Pages 287-295Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2013.09.038
Keywords
Pincer compounds; Palladium compounds; Suzuki-Miyaura couplings; Catalysis; Crystal structures; Iminophosphoranes
Categories
Funding
- DGAPA-UNAM [IN201711-3]
- CONACYT [CB2009/134528, CB2010/154732]
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The iminophosphorane ligands (Ph3P=NC6H4SR) [R = CH3 (1) and C6H5 (2)] were easily synthesized from triphenylphosphine and 2-(methylthio)aniline or 2-(phenylthio) aniline respectively by the Horner and Oediger variation of the Kirsanov reaction. The reactivity of both ligands was explored with [Na2PdCl4] to afford the corresponding non-symmetric iminophosphorane pincer derivatives [PdCl{C6H4(Ph2P=NC6H4SR-kappa(3)-C,N,S)}] [R = CH3 (3) and C6H5 (4)]. A careful monitoring of the reaction by P-31 {H-1} NMR experiments revealed the N, S chelated species [PdCl2{C6H4(Ph2P=NC6H4SR-kappa(2)-N,S)}] [R = CH3 (5) and C6H5 (6)] to be stable intermediates through the formation of the pincer compounds. Thus, carrying out the reaction for the attaining of (4) at room temperature allowed the isolation and full characterization of the chelated complex [PdCl2{C6H4(Ph2P=NC6H4SPh-kappa-N,S)}] (6). All above mentioned species were unequivocally characterized by single crystal X-ray diffraction experiments. In addition, the newly synthesized pincer complexes [PdCl{C6H4(Ph2P=NC6H4SR-kappa(3)-C,N,S)}] [R = CH3 (3) and C6H5 (4)] were tested as catalyst, proven to be efficient in the Suzuki-Miyaura C-C cross coupling reactions of a series of para-substituted bromobenzenes. (C) 2013 Elsevier B. V. All rights reserved.
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