In situ phosphonium-containing Lewis basecatalyzed 1,6-cyanation reaction:a facile way to obtainα-diaryl andα-triaryl acetonitriles  

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作  者:Jian-Ping Tan Yuan Chen Xiaoyu Ren Yumeng Guo Bing Yi Hongkui Zhang Guowei Gao Tianli Wang 

机构地区:[1]Hunan Province Key Laboratory of Environmental Catalysis and Waste Recycling,College of Materials and Chemical Engineering,Hunan Institute of Engineering,Xiangtan,411104,P.R.China [2]Key Laboratory of Green Chemistry&Technology of Ministry of Education,College of Chemistry,Sichuan University 29 Wangjiang Road,Chengdu 610064,P.R.China

出  处:《Organic Chemistry Frontiers》2022年第1期156-162,共7页有机化学前沿(英文)

基  金:support was provided by the National Natural Science Foundation of China(21971165,21921002,21772035,22101189);National Key R&D Program of China(2018YFA0903500);National Natural Science Foundation of Hunan(2021JJ40150).

摘  要:We present a phosphonium-containing catalyst generated in situ from phosphine and tert-butyl acrylate that serves as an unusual Lewis base catalyst.It was applied for the promotion of a remote 1,6-cyanation reaction of p-quinone methides and fuchsones employing trimethylsilyl cyanide as the cyanide source.A diverse range ofα-diaryl andα-triaryl acetonitriles was obtained in high yields under mild reaction conditions with low catalyst loading(5 mol%).The practicality and utility of this protocol were demonstrated via the gram-scale preparation and facile elaboration of products.Mechanistic investigations(in situ NMR and ESI-MS analysis)were employed to characterize the active zwitterionic phosphonium intermediate,which was the“true”active catalyst.

关 键 词:catalyst FACILE ACETONITRILE 

分 类 号:O62[理学—有机化学]

 

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