{"title":"Catalyst-Controlled Regiodivergent C–H Alkynylation of 2-Pyridylthiophenes","authors":"Yuting Gui, Yaokun Zhao, Xingchi Li, Taoyuan Liang, Shuangliang Zhao, Zhuan Zhang","doi":"10.1002/adsc.202400856","DOIUrl":null,"url":null,"abstract":"Different catalysts are presented to overcome or augment a substrate’s innate regioselectivity. Rhodium was found to overcome the innate C3-selectivity <i>via</i> chelation-assisted rhodation. Conversely, palladium was found to enhance the innate C5-selectivity <i>via </i>electrophilic palladation. These reactions allow for the formation of a diverse range of synthetically versatile C3- and C5-alkynylated products from 2-pyridylthiophenes. Notably, this strategy was successfully employed in the straightforward synthesis of π-extended functionalized 2-pyridylthiophenes, which could be converted into more valuable compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202400856","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Different catalysts are presented to overcome or augment a substrate’s innate regioselectivity. Rhodium was found to overcome the innate C3-selectivity <i>via</i> chelation-assisted rhodation. Conversely, palladium was found to enhance the innate C5-selectivity <i>via </i>electrophilic palladation. These reactions allow for the formation of a diverse range of synthetically versatile C3- and C5-alkynylated products from 2-pyridylthiophenes. Notably, this strategy was successfully employed in the straightforward synthesis of π-extended functionalized 2-pyridylthiophenes, which could be converted into more valuable compounds.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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