Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki-Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

被引:24
作者
Shaik, Jeelani Basha [1 ]
Ramkumar, Venkatachalam [1 ]
Varghese, Babu [2 ]
Sankararaman, Sethuraman [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India
[2] Indian Inst Technol, Sophisticated Analyt Instrument Facil, Madras 600036, Tamil Nadu, India
关键词
C-C coupling; N-heterocyclic carbene; palladium; Suzuki-Miyaura coupling; 1,2,3-triazolylidene; N-HETEROCYCLIC CARBENES; PALLADIUM COMPLEXES; LIGANDS;
D O I
10.3762/bjoc.9.79
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki-Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and with high turnover numbers. With 1,4-dibromobenzene the catalyst was found to be active for up to 13 consecutive cycles with a turnover number of 1260. The polyarylarenes were obtained in pure form after crystallization once without recourse to chromatographic purification. The single-crystal X-ray structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl-1,2,3- triazol-5-ylidene as the ligand.
引用
收藏
页码:698 / 704
页数:7
相关论文
共 33 条
[31]   Robust Acenaphthoimidazolylidene Palladium Complexes: Highly Efficient Catalysts for Suzuki-Miyaura Couplings with Sterically Hindered Substrates [J].
Tu, Tao ;
Sun, Zheming ;
Fang, Weiwei ;
Xu, Mizhi ;
Zhou, Yunfei .
ORGANIC LETTERS, 2012, 14 (16) :4250-4253
[32]   1,2,3-Triazolin-5-ylidenes: Synthesis of Hetero-bis(carbene) Pd(II) Complexes, Determination of Donor Strengths, and Catalysis [J].
Yuan, Dan ;
Huynh, Han Vinh .
ORGANOMETALLICS, 2012, 31 (01) :405-412
[33]  
Zhang HJ, 2006, CHEM COMMUN, P755, DOI 10.1039/b515433b