Abstract
A new quinoline-based Pd(II)-complex was synthesized and its structure was established by single crystal X-ray analysis. Applications of the obtained complex as a precatalyst in SuzukiMiyaura C-C cross-coupling reactions of 4-bromoacetophenone and 5-bromobenzofuran-2carboxylate esters with several aryl- and heteroarylboronic acids were investigated. The catalytic activity of the Pd(II)-precatalyst under microwave irradiating conditions was evaluated.
Highlights
Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids,[1,2,3,4] is one of the most valuable synthetic routes for the preparation of symmetric and asymmetric biaryls, which are important skeletons in the structures of biologically active compounds,[5] agrochemicals, pharmaceuticals,[6,7,8] polymers,[9] ligands,[10] and functional materials.[11]
In continuation of our recent research work concerned on the use of Pd(II)-complexes as precatalysts in C-C cross coupling reactions in aqueous media under microwave irradiation conditions,[27,28,29,30,31,32,33,34,35,36] and on the chemistry of 2- and 3-substituted benzofuran derivatives,[37,38,39] we report here the synthesis of the new Pd(II)-complex 3 to evaluate its catalytic activity in the Suzuki-Miyaura cross-coupling arylation of 5-bromobenzofuran-2-carboxylate esters 7 and 15
Complex 3 was found as an effective precatalyst for the coupling of 5bromobenzofuran-2-carboxylate esters 7 and 15 for the synthesis of new 5-arylbenzofran-2carboxylates
Summary
Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids,[1,2,3,4] is one of the most valuable synthetic routes for the preparation of symmetric and asymmetric biaryls, which are important skeletons in the structures of biologically active compounds,[5] agrochemicals, pharmaceuticals,[6,7,8] polymers,[9] ligands,[10] and functional materials.[11]. 30 30 25 15 a Reaction conditions: Bromide/ boronic acid/ base/ TBAB/ solvent (3 mL): 1/1.2/2/0.6, microwave irradiation (200 Watt) at 150 oC for 2 min.
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