{"title":"General Modular and Convergent Approach to Diversely Functionalized Allylic Systems.","authors":"Sachin Giri, Nikita Kvasovs, Vladimir Gevorgyan","doi":"10.1021/jacs.5c02866","DOIUrl":null,"url":null,"abstract":"<p><p>Synthesis of allylic functionalized motifs forging C-O, C-C, and C-S bonds has been achieved via visible-light-induced palladium catalysis. Simple alkenes, readily available 1,1-dielectrophiles, and commercially available nucleophiles are directly coupled in a sequential manner to construct a diverse array of medicinally relevant complex molecules. Unlike the classical Tsuji-Trost reaction, this protocol eliminates the need for prefunctionalized starting materials, offering a much more general and modular approach with options for stereoselective reactions. Additionally, inherent synthetic challenges associated with oxygen-, carbon-, and sulfur-based nucleophiles are addressed, thus establishing a versatile toolkit for accessing allylic ethers, esters, sulfones, and alkylated motifs.</p>","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":" ","pages":""},"PeriodicalIF":14.4000,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.5c02866","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Synthesis of allylic functionalized motifs forging C-O, C-C, and C-S bonds has been achieved via visible-light-induced palladium catalysis. Simple alkenes, readily available 1,1-dielectrophiles, and commercially available nucleophiles are directly coupled in a sequential manner to construct a diverse array of medicinally relevant complex molecules. Unlike the classical Tsuji-Trost reaction, this protocol eliminates the need for prefunctionalized starting materials, offering a much more general and modular approach with options for stereoselective reactions. Additionally, inherent synthetic challenges associated with oxygen-, carbon-, and sulfur-based nucleophiles are addressed, thus establishing a versatile toolkit for accessing allylic ethers, esters, sulfones, and alkylated motifs.
期刊介绍:
The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.