The generation of new metal complexes with potentially interesting properties provides the motivation for designing novel polydentate bridging ligands. Herein we report the syntheses of tertiary indolylphenylphosphines L, where L ) diphenyl(3-methyl-2-indolyl)phosphine (P(C 6 H 5 ) 2 (C 9 H 8 N), 1), phenylbis(3-methyl-2-indolyl)phosphine (P(C 6 H 5 )(C 9 H 8 N) 2 , 2), and bis(1H-3-indolyl)methane-(2,12)-phenylphosphine (P(C 6 H 5 )(C 17 H 12 N 2 ), 3). Ligands 1-3 were functionalized at the indolyl nitrogen with a variety of both electron-withdrawing and electron-donating groups. The solid-state structures of 1, 2, and N-functionalized indolylphosphines diphenyl(3-methyl-1-benzyl-2-indolyl)phosphine (P(C 6 H 5 ) 2 (C 9 H 7 N(CH 2 C 6 H 5 )), N-Bz-1) and bis[1-(CH 2 C 6 F 5 )-3-indolyl]methane-(2,12)-phenylphosphine (P(C 6 H 5 )(C 17 H 10 N 2 [CH 2 C 6 F 5 ] 2 ), (N-F 5 Bz) 2 -3), are reported. The reaction of ligands 1-3 with 1 equiv of Pd(COD)Cl 2 led to the formation of Pd(II) complexes of the type [Pd(L)Cl(µ-Cl)] 2 (4, L ) 1; 5, L ) 2; 6, L ) 3). The products were characterized by 1 H, 13 C, and 31 P NMR spectroscopy, mass spectrometry, and elemental analysis. X-ray crystallography established the dimeric structure of the products and confirmed the ability of the ligands to serve, in the absence of base, as monodentate P-donors in reaction with a transition metal. The indolyl NH groups of the complexes 4-6 demonstrate a marked propensity for hydrogen bonding in the solid state.

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