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Di‐ and Tetranuclear Palladium(II) Complexes Containing C,N‐Bidentate Furoylhydrazone for Suzuki–Miyaura Reactions
Author(s) -
Qian Hengyu,
Zhang Tongyan,
Song Liping,
Yu Shuyan,
Yuan Qi,
Sun Luyan,
Zhang Dengfeng,
Yin Zhigang,
Dai Yongxia
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700027
Subject(s) - chemistry , palladium , denticity , phenylboronic acid , medicinal chemistry , aryl , ligand (biochemistry) , halide , stereochemistry , crystal structure , catalysis , crystallography , organic chemistry , biochemistry , alkyl , receptor
Furoylhydrazones of general formula 4‐R–C 6 H 4 –CH=NNH–CO–2‐C 4 H 3 O [R = H (HL1) and OCH 3 (HL2)] have been conveniently prepared from furan‐2‐carbohydrazide. The reaction of HL1 with Li 2 [PdCl 4 ] and CH 3 COONa provided the di‐µ‐chloro‐bridged cyclopalladated complex [Pd(C 6 H 4 –CH=N–NH–CO–2‐C 4 H 3 O)(µ‐Cl)] 2 ( 1 ) through aryl C–H bond activation, whereas the unusual tetranuclear cluster [Pd(4‐CH 3 O–C 6 H 4 –CH=N–NH–CO–2‐C 4 H 3 O)(µ‐Cl)] 4 ( 2 ) was obtained from the reaction with ligand HL2. The crystal structures of 1 and 2 show a slightly distorted square‐planar coordination geometry around the palladium ion to which the furoylhydrazone is attached in a bidentate fashion. The two palladium(II) complexes were able to catalyze the Suzuki–Miyaura coupling reactions of phenylboronic acid with aryl halides to afford the desired biaryl derivatives in excellent yields (up to 99.2 %).