Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene | |
Department | 羰基合成与选择氧化国家重点实验室(OSSO) |
Li Yang; Lijun Shi; Chungu Xia; Li FW(李福伟) | |
The second department | 清洁催化与合成 |
2020-07 | |
Source Publication | Chinese Journal of Catalysis |
Volume | 41Issue:7Pages:1152 |
Abstract | An efficient route for the palladium-catalyzed reductive aminocarbonylation of olefins with nitroarenes was developed using carbon monoxide (CO) as both reductant and carbonyl source, which enables facile access to amides with excellent regioselectivity and broad substrate scope. It is found that the counter anions of the Pd catalyst precursors significantly affect the reaction chemoselectivity and amide regioselectivity. Branched amides were mainly obtained with K2PdCl4 as the metal catalyst, and phosphine ligands had no influence on the regioselectivity but affected the catalytic reactivity. However, phosphine ligands had significant effects on aminocarbonylation regioselectivity when Pd(CH3CN)4(OTf)2 was used; monodentate phosphines tended to form branched amides, and bidentate phosphines mainly formed linear amides. Trapping experiments, primary kinetic studies, and control reactions with all possible N-species reduced from nitroarene indicated that the catalytic synthesis of branched and linear amides produced nitrene (further converted to enamide) and aniline, respectively, different from the previous ligand-controlled regioselective synthesis of amides via the aminocarbonylation of olefins with amines. Furthermore, the proposed synthesis route could be applied in the synthesis of gram-scale propanil under mild conditions. |
DOI | 10.1016/S1872-2067(20)63561-6 |
Indexed By | SCI |
If | 6.1 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/27052 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Chungu Xia; Li FW(李福伟) |
Affiliation | 中国科学院兰州化学物理研究所 |
Recommended Citation GB/T 7714 | Li Yang,Lijun Shi,Chungu Xia,et al. Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene[J]. Chinese Journal of Catalysis,2020,41(7):1152. |
APA | Li Yang,Lijun Shi,Chungu Xia,&Li FW.(2020).Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene.Chinese Journal of Catalysis,41(7),1152. |
MLA | Li Yang,et al."Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene".Chinese Journal of Catalysis 41.7(2020):1152. |
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