Publication History Received14 December 1995Published online11 June 1996Published inissue 11 June 1996

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The complex(es) resulting from a 1:4 mixture of Pd2(DBA)3 and P(o-tol)3 react with aryl bromides or aryl iodides p-XC6H4R (X = Br, I; R = Me, t-Bu, OMe) to generate the corresponding halide dimers {Pd(p-C6H4R)(μ-X)}2 (X = Br, R = t-Bu (1), Me (2), OMe (3); X = I, R = t-Bu (4), Me (5), OMe (6)) in 46−76% yield. Iodide dimer 5 reacts with AgOTf in acetonitrile to form the cationic bis(acetonitrile) complex {Pd(p-C6H4Me)(CH3CN)2>}+OTf- (8) which was treated in situ with LiCl to form the chloride dimer {Pd(p-C6H4Me)(μ-Cl)}2 (9) in 93% yield. The p-tolyl halide dimers 2, 5, and 9 react with N-benzylmethylamine to generate the corresponding 1:1 palladium amine adducts Pd(p-C6H4Me)X (X = Cl (12), 85%; X = Br (13), 72%; X = I (14), 77%). Reaction of a mixture of Pd2(DBA)3 and P(o-tol)3 with the haloamines 2-IC6H4(CH2)2N(H)Bn, 2-BrC6H4CH2N(H)(p-tolyl), and 2-BrC6H4(CH2)3N(H)Bn gave the chelated palladium amine complexes Pd(2-C6H4(CH2)2N(H)Bn>I (18, 71%), Pd<2-C6H4CH2N(H)(p-tolyl)>Br (19, 77%), and Pd(2-C6H4(CH2)3N(H)Bn>Br (21, 24%), respectively. Variable-temperature 1H and 31P NMR analysis of 1214 and related complexes was consistent with hindered rotation about the P−C bonds, with predominant formation of the exo2-P(o-tol) conformer, and hindered rotation about the Pd−P bond with formation of three unequally populated rotamers.


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