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Synthesis and characterization of transition metal complexes of thiophene‐2‐methylamine: X‐ray crystal structure of palladium (II) and platinum (II) complexes and use of palladium(II) complexes as pre‐catalyst in Heck and Suzuki cross‐coupling reactions
Author(s) -
Aydemir Murat,
Baysal Akın,
Durap Feyyaz,
Gümgüm Bahattin,
Özkar Saim,
Yıldırım Leyla Tatar
Publication year - 2009
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1547
Subject(s) - chemistry , palladium , methylamine , platinum , phosphine , transition metal , thiophene , catalysis , medicinal chemistry , crystal structure , heck reaction , stereochemistry , crystallography , organic chemistry
The reactions of thiophene‐2‐( N ‐diphenylphosphino)methylamine, Ph 2 PNHCH 2 ‐C 4 H 3 S, 1 and thiophene‐2‐[ N , N ‐bis(diphenylphosphino)methylamine], (Ph 2 P) 2 NCH 2 ‐C 4 H 3 S, 2, with MCl 2 (cod) (M = Pd, Pt; cod = 1,5‐cyclooctadiene) or [Cu(CH 3 CN) 4 ]PF 6 yields the new complexes [M(Ph 2 PNHCH 2 ‐C 4 H 3 S) 2 Cl 2 ], M = Pd 1a, Pt 1b, [Cu(Ph 2 PNHCH 2 ‐C 4 H 3 S) 4 ]PF 6 , 1c, and [M(Ph 2 P) 2 NCH 2 ‐C 4 H 3 S)Cl 2 ], M = Pd 2a, Pt 2b, {Cu[(Ph 2 P) 2 NCH 2 ‐C 4 H 3 S] 2 }PF 6 , 2c, respectively. The new compounds were isolated as analytically pure crystalline solids and characterized by 31 P‐, 13 C‐, 1 H‐NMR and IR spectroscopy and elemental analysis. Furthermore, the solid‐state molecular structures of representative palladium and platinum complexes of bis(phosphine)amine, 2a and 2b, respectively, were determined using single crystal X‐ray diffraction analysis. The palladium complexes were tested as potential catalysts in the Heck and Suzuki cross‐coupling reactions. Copyright © 2009 John Wiley & Sons, Ltd.