| Autor: |
Yumeng Guo, Bing Yi, Jian-Ping Tan, Tian Li Wang, Hongkui Zhang, Guowei Gao, Yuan Chen, Xiaoyu Ren |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Organic Chemistry Frontiers. 9:156-162 |
| ISSN: |
2052-4129 |
| DOI: |
10.1039/d1qo01501j |
| Popis: |
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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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