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Direct C–H heteroarylation by an acenaphthyl-based α-diimine palladium complex: improvement of the reaction efficiency for bi(hetero)aryls under aerobic conditions
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2017-08-28 00:00:00 , DOI: 10.1039/c7qo00562h
Fu-Min Chen 1, 2, 3, 4, 5 , Fei-Dong Huang 1, 2, 3, 4, 5 , Xue-Yi Yao 1, 2, 3, 4, 5 , Tian Li 1, 2, 3, 4, 5 , Feng-Shou Liu 1, 2, 3, 4, 5
Affiliation  

A bulky ancenaphthyl skeleton-based α-diimine palladium complex with ortho-tert-butyl on N-aryl moieties was designed, synthesized and characterized. The developed palladium complex was applied for direct C–H arylation under aerobic reaction conditions. A range of heteroaryls, such as thiozoles, thiophenes, furans, imidazopyridines, indolizines, isoxazoles, imidazoles, triazoles, pyrazoles, indoles, pyrroles and pyrazolidinones, were used, while various coupling partners of heteroaryl bromides with wide functional groups were compatible. Upon using 0.1–0.05 mol% of a precatalyst, more than 90 examples of cross-coupling products were afforded in good to excellent yields, demonstrating that this phosphine-free catalytic system scaffold enables a general access to biheteroaryls.

中文翻译:

通过C基的α-二亚胺钯配合物直接进行CH杂芳基化:提高好氧条件下双(杂)芳基的反应效率

设计,合成和表征了大体积的基于萘基骨架的α-二亚胺钯配合物,在N-芳基部分上带有邻-叔丁基。发达的钯配合物在好氧反应条件下用于直接的CHH芳基化反应。使用了各种杂芳基,例如噻唑,噻吩,呋喃,咪唑并吡啶,吲哚利嗪,异恶唑,咪唑,三唑,吡唑,吲哚,吡咯和吡唑烷酮,而具有宽泛官能团的杂芳基溴化物的各种偶联伙伴是相容的。当使用0.1-0.05 mol%的预催化剂时,提供了90多个实例的交叉偶联产物,收率良好至极佳,这表明这种无膦的催化体系支架能够普遍使用双杂芳基。
更新日期:2017-09-05
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