In situ phosphonium-containing Lewis base-catalyzed 1,6-cyanation reaction: a facile way to obtain α-diaryl and α-triaryl acetonitriles

文献情報

出版日 2021-11-11

DOI 10.1039/D1QO01501J

インパクトファクター 5.281

著者

Yuan Chen, Xiaoyu Ren, Yumeng Guo, Bing Yi, Hongkui Zhang, Guowei Gao, Tianli Wang

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要旨

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 of α-diaryl and α-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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

In situ phosphonium-containing Lewis base-catalyzed 1,6-cyanation reaction: a facile way to obtain α-diaryl and α-triaryl acetonitriles

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