{"title":"Regioselective Alkylacylation of 1,3-Dienes by Merging N-Heterocyclic Carbene Catalysis with Photoinduced Palladium Catalysis","authors":"Ying Huang, You-Feng Han, Chun-Lin Zhang, Song Ye","doi":"10.1021/acs.orglett.4c04453","DOIUrl":null,"url":null,"abstract":"Herein, we develop a dual catalytic platform for the 1,2- or 1,4-alkylacylation reaction of 1,3-dienes with readily available alkyl halides and aldehydes by merging <i>N</i>-heterocyclic carbene catalysis with photoinduced palladium catalysis. A series of β,γ-unsaturated ketones are obtained in good to high yields. Mechanistic studies suggest that this reaction involves a radical process. The direct synthesis of flavanone from salicylaldehyde exemplified the potential capability of this dual catalytic platform.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"12 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04453","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Regioselective Alkylacylation of 1,3-Dienes by Merging N-Heterocyclic Carbene Catalysis with Photoinduced Palladium Catalysis
Herein, we develop a dual catalytic platform for the 1,2- or 1,4-alkylacylation reaction of 1,3-dienes with readily available alkyl halides and aldehydes by merging N-heterocyclic carbene catalysis with photoinduced palladium catalysis. A series of β,γ-unsaturated ketones are obtained in good to high yields. Mechanistic studies suggest that this reaction involves a radical process. The direct synthesis of flavanone from salicylaldehyde exemplified the potential capability of this dual catalytic platform.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.