Reactivity of 4-phenylthiazoles in ruthenium catalyzed direct arylations

被引：3

作者：

Daher, Ahmad ^{[1
]}

Jacquemin, Denis ^{[2
]}

Guerchais, Veronique ^{[1
]}

Soule, Jean-Francois ^{[1
]}

Doucet, Henri ^{[1
]}

机构：

[1] Univ Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France

[2] Univ Nantes, CNRS, CEISAM UMR 6230, 2 Rue Houssiniere, F-44322 Nantes 03, France

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2019年 / 33卷 / 04期

关键词：

arylation; C-C bond formation; C-H bond activation; palladium; ruthenium; H BOND FUNCTIONALIZATION; HIGHLY EFFICIENT; CHIRAL SULFONES; ACTIVATION; HETEROARENES; CARBOXYLATE; COMPLEXES; PARAMETERS; THIAZOLES; MECHANISM;

D O I：

10.1002/aoc.4794

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The reactivity of the phenyl substituent of 4-phenylthiazoles in Ru-catalyzed direct arylation was studied. 4-Phenylthiazole was found to be unreactive; whereas, the introduction of an aryl unit at C5-position of 4-phenylthiazole enhances its reactivity, allowing the selective mono-arylation of the phenyl unit of 4-phenylthiazoles in moderate to high yields using 5 mol% of [Ru(p-cymene)Cl-2](2) catalyst precursor associated to KOPiv as base. These results reveal that the conformation and electronic properties of 4-phenylthiazoles are crucial to allow the formation of suitable intermediates in the course of the catalytic cycle. The reaction tolerated both electron-rich and electron-poor aryl bromides allowing the straightforward tuning of the electronic properties of the arylated 2-methyl-4-phenyl-5-arylthiazoles.

引用

页数：11

共 47 条

[31] C-H bond functionalisation with [RuH(codyl)2]BF4 catalyst precursor [J].

Li, Wenbo ;

Arockiam, Percia B. ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

GREEN CHEMISTRY, 2011, 13 (09) :2315-2319

[32] RuCl3•xH2O-Catalyzed Direct Arylation of Arenes with Aryl Chlorides in the Presence of Triphenylphosphine [J].

Luo, Ning ;

Yu, Zhengkun .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (03) :787-791

[33] Direct arylation of imidazo[2,1-b]thiazoles and thiazoles with aryl iodides via CuCl2/PPh3-catalyzed C-H bond functionalization [J].

Ma, Yuchang ;

Na, Min ;

Gu, Yanfang ;

Huang, Guoli ;

Li, Xia ;

Chen, Yegao .

APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (03) :165-169

[34] Excimer Emission in Single Layer Electroluminescent Devices Based on [Ir(4,5-diphenyl-2-methylthiazolo)2(5-methyl-1,10-phenanthroline)]+ [PF6]- [J].

Margapoti, E. ;

Shukla, V. ;

Valore, A. ;

Sharma, A. ;

Dragonetti, C. ;

Kitts, C. C. ;

Roberto, D. ;

Murgia, M. ;

Ugo, R. ;

Muccini, M. .

JOURNAL OF PHYSICAL CHEMISTRY C, 2009, 113 (28) :12517-12522

[35] Ruthenium complex-catalyzed direct ortho arylation and alkenylation of 2-arylpyridines with organic halides [J].

Oi, S ;

Fukita, S ;

Hirata, N ;

Watanuki, N ;

Miyano, S ;

Inoue, Y .

ORGANIC LETTERS, 2001, 3 (16) :2579-2581

[36] Ortho-selective Arylation of Arylazoles with Aryl Bromides Catalyzed by Ruthenium Complexes [J].

Oi, Shuichi ;

Sasamoto, Hiromi ;

Funayama, Raito ;

Inoue, Yoshio .

CHEMISTRY LETTERS, 2008, 37 (09) :994-995

[37] Bulky α-diimine palladium complexes: highly efficient for direct C-H bond arylation of heteroarenes under aerobic conditions [J].

Ouyang, Jia-Sheng ;

Li, Yan-Fang ;

Shen, Dong-Sheng ;

Ke, Zhuofeng ;

Liu, Feng-Shou .

DALTON TRANSACTIONS, 2016, 45 (38) :14919-14927

[38] An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation [J].

Peters, Byron K. ;

Zhou, Taigang ;

Rujirawanich, Janjira ;

Cadu, Alban ;

Singh, Thishana ;

Rabten, Wangchuk ;

Kerdphon, Sutthichat ;

Andersson, Pher G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (47) :16557-16562

[39]

Ravikiran C. G., 2014, CHEM COMMUN, V50, P2442

[40] NEW COUMARIN DYES WITH RIGIDIZED STRUCTURE FOR FLASHLAMP-PUMPED DYE LASERS [J].

REYNOLDS, GA ;

DREXHAGE, KH .

OPTICS COMMUNICATIONS, 1975, 13 (03) :222-225

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