{"title":"光氧化还原辅助酮与芳烯直接a-烷基化反应的研究","authors":"Tsubasa Hirata, Tomoya Hisada, Yoshihiro Ogasawara, Shū Kobayashi, Yasuhiro Yamashita","doi":"10.1002/hlca.202300139","DOIUrl":null,"url":null,"abstract":"<p>Photoinduced direct α-alkylation reactions of ketones with arylalkenes using an organophotocatalyst and a Brønsted base were developed. It was found that the choice of both Brønsted base and photocatalyst was crucial, and in the presence of catalytic amounts of 2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) and LiO<sup><i>t</i></sup>Bu, the desired reactions of ketones with styrene analogues proceeded smoothly under blue-LED light irradiation to afford the products in moderate to high yields. This method constitutes an atom-economical alkylation process for α-functionalization of both cyclic and acyclic ketones.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 1","pages":""},"PeriodicalIF":1.5000,"publicationDate":"2023-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300139","citationCount":"0","resultStr":"{\"title\":\"Development of Photoredox-Assisted Direct α-Alkylation Reactions of Ketones with Arylalkenes Using a Catalytic Amount of LiOtBu as a Brønsted Base\",\"authors\":\"Tsubasa Hirata, Tomoya Hisada, Yoshihiro Ogasawara, Shū Kobayashi, Yasuhiro Yamashita\",\"doi\":\"10.1002/hlca.202300139\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Photoinduced direct α-alkylation reactions of ketones with arylalkenes using an organophotocatalyst and a Brønsted base were developed. It was found that the choice of both Brønsted base and photocatalyst was crucial, and in the presence of catalytic amounts of 2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) and LiO<sup><i>t</i></sup>Bu, the desired reactions of ketones with styrene analogues proceeded smoothly under blue-LED light irradiation to afford the products in moderate to high yields. This method constitutes an atom-economical alkylation process for α-functionalization of both cyclic and acyclic ketones.</p>\",\"PeriodicalId\":12842,\"journal\":{\"name\":\"Helvetica Chimica Acta\",\"volume\":\"107 1\",\"pages\":\"\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2023-11-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300139\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Helvetica Chimica Acta\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202300139\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Helvetica Chimica Acta","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202300139","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Development of Photoredox-Assisted Direct α-Alkylation Reactions of Ketones with Arylalkenes Using a Catalytic Amount of LiOtBu as a Brønsted Base
Photoinduced direct α-alkylation reactions of ketones with arylalkenes using an organophotocatalyst and a Brønsted base were developed. It was found that the choice of both Brønsted base and photocatalyst was crucial, and in the presence of catalytic amounts of 2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) and LiOtBu, the desired reactions of ketones with styrene analogues proceeded smoothly under blue-LED light irradiation to afford the products in moderate to high yields. This method constitutes an atom-economical alkylation process for α-functionalization of both cyclic and acyclic ketones.
期刊介绍:
Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.