{"title":"Copper-Catalyzed Regioselective Cyanation/Diarylmethylation of Formamides: Construction of α-Cyano Functionalized Tetra-Substituted Olefins","authors":"Minjing Yuan, Zikang Li, Weifeng Xu, Biquan Xiong, Yu Liu, Min Liu, Ke-Wen Tang, Longzhi Zhu","doi":"10.1002/cjoc.202400911","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>A copper-catalyzed cyanation/diarylmethylation of formamides has been developed for the synthesis of α-cyano functionalized tetra-substituted olefins by utilizing <i>para</i>-quinone methides (<i>p</i>-QMs) and trimethylcyanosilane as functionalization sources. Various kinds of <i>p</i>-QMs and formamides are well tolerated, delivering the desired products with 72%—94% yields, demonstrating broad functional group tolerance. Notably, the reaction does not require noble metals and proceeds regioselectively under mild conditions. Based on step-by-step control experiments, Hammett studies and DFT calculation, a plausible mechanism is proposed.</p><p>\n </p>\n </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"191-198"},"PeriodicalIF":5.5000,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.202400911","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A copper-catalyzed cyanation/diarylmethylation of formamides has been developed for the synthesis of α-cyano functionalized tetra-substituted olefins by utilizing para-quinone methides (p-QMs) and trimethylcyanosilane as functionalization sources. Various kinds of p-QMs and formamides are well tolerated, delivering the desired products with 72%—94% yields, demonstrating broad functional group tolerance. Notably, the reaction does not require noble metals and proceeds regioselectively under mild conditions. Based on step-by-step control experiments, Hammett studies and DFT calculation, a plausible mechanism is proposed.
期刊介绍：
The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.
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