Well-Defined N-Heterocyclic Carbene-Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C-H bond Arylation of Benzothiazole

被引：17

作者：

Yadav, Seema ^{[1
]}

Singh, Ajeet ^{[2
]}

Mishra, Isha ^{[1
]}

Ray, Sriparna ^{[3
]}

Mobin, Shaikh M. ^{[2
]}

Dash, Chandrakanta ^{[1
]}

机构：

[1] Cent Univ Rajasthan, Sch Chem Sci & Pharm, Dept Chem, Bandarsindri, India

[2] Indian Inst Technol IIT Indore, Dept Chem, Khandwa Rd, Indore 453552, Madhya Pradesh, India

[3] Manipal Univ Jaipur, Sch Basic Sci, Dept Chem, Jaipur 303007, Rajasthan, India

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2019年 / 33卷 / 07期

关键词：

benzofuran derivatives; C-H arylation; N-heterocyclic carbene; palladium; PEPPSI; CROSS-COUPLING REACTIONS; PD-NHC PRECATALYST; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; PEPPSI COMPLEXES; BENZOFURAN DERIVATIVES; MECHANISTIC INSIGHTS; PINCER COMPLEXES; ARYL BROMIDES; COPPER;

D O I：

10.1002/aoc.4936

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Well-defined and air-stable PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed palladium bis-N-heterocyclic carbene complexes have been developed for the domino Sonogashira coupling/cyclization reaction of 2-iodophenol with a variety of terminal alkynes and C-H bond arylation of benzothiazole with aryl iodides. The PEPPSI themed palladium complexes, 2a and 2b were synthesized in good yields from the reaction of corresponding imidazolium salts with PdCl2 and K2CO3 in pyridine. The new air-stable palladium-NHC complexes were characterized by NMR spectroscopy, X-ray crystallography, elemental analysis, and mass spectroscopy studies. The PEPPSI themed palladium(II) bis-N-heterocyclic carbene complexes 2a and 2b exhibited excellent catalytic activities for domino Sonogashira coupling/cyclization reaction of 2-iodophenol with terminal alkynes yielding benzofuran derivatives. In addition, the palladium complexes, 2a and 2b successfully catalyzed the direct C-H bond arylation of benzothiazole with aryl iodides as coupling partners in presence of CuI as co-catalyst.

引用

页数：11

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