M. Aydemir, A. Baysal, N. Gürbüz
Nov 26, 2009
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0
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24
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Journal
Applied Organometallic Chemistry
Abstract
Three new (N-diphenylphosphino)-isopropylanilines, having isopropyl substituent at the carbon 2- (1) 4- (2) or 2,6- (3) were prepared from the aminolysis of chlorodiphenylphosphine with 2-isopropylaniline, 4-isopropylaniline or 2,6-diisopropylaniline, respectively, under anaerobic conditions. Oxidation of 1,2 and 3 with aqueous hydrogen peroxide, elemental sulfur or gray selenium gave the corresponding oxides, sulfides and selenides (Ph2PE)NHC6H42-CH(CH3)2, (Ph2PE)NHC6H44-CH(CH3)2 and (Ph2PE)NHC6H42,6-{CH(CH3)2}2, where E = O, S, or Se, respectively. The reaction of [M(cod)Cl2] (M = Pd, Pt; cod = 1,5-cyclooctadiene) with two equivalents of 1,2 or 3 yields the corresponding monodendate complexes [M((Ph2P)NHC6H42-CH(CH3)2)2Cl2], M = Pd 1d, M = Pt 1e, [M((Ph2P)NHC6H44-CH(CH3)2)2Cl2], M = Pd 2d, M = Pt 2e and [M((Ph2P)NHC6H42,6-(CH(CH3)2)2)2Cl2], M = Pd 3d, M = Pt 3e, respectively. All the compounds were isolated as analytically pure substances and characterized by NMR, IR spectroscopy and elemental analysis. Furthermore, representative solid-state structure of [(Ph2PS)NHC6H44-CH(CH3)2] (2b) was determined using single crystal X-ray diffraction technique. The complexes 1d–3d were tested and found to be highly active catalysts in the Suzuki coupling and Heck reaction, affording biphenyls and stilbenes, respectively. Copyright © 2009 John Wiley & Sons, Ltd.