{"title":"由光促成的酮、卤素原子转移(XAT)和镍介导的 C(sp3)-C(sp2)交叉亲电偶联的协同合并","authors":"Alisha Rani Tripathy, Akash Bisoyi, Arya P, Sreelakshmi Venugopal and Veera Reddy Yatham*, ","doi":"10.1021/acsorginorgau.3c00062","DOIUrl":null,"url":null,"abstract":"<p >In the present manuscript, we have developed a unique catalytic system by merging photoexcited ketone catalysis, halogen atom transfer (XAT), and nickel catalysis to forge C(sp<sup>3</sup>)–C(sp<sup>2</sup>) cross-electrophile coupling products from unactivated iodoalkanes and (hetero)aryl bromides. The synergistic catalytic system works under mild reaction conditions and tolerates a variety of functional groups; moreover, this strategy allows the late-stage modification of medicinally relevant molecules. Preliminary mechanistic studies reveal the role of the α-aminoalkyl radical, which further participates in the XAT process with alkyl iodides to generate the desired alkyl radical, which eventually intercepts with the nickel catalytic cycle to liberate the products in good to excellent yields.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2023-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00062","citationCount":"0","resultStr":"{\"title\":\"Synergistic Merger of Ketone, Halogen Atom Transfer (XAT), and Nickel-Mediated C(sp3)–C(sp2) Cross-Electrophile Coupling Enabled by Light\",\"authors\":\"Alisha Rani Tripathy, Akash Bisoyi, Arya P, Sreelakshmi Venugopal and Veera Reddy Yatham*, \",\"doi\":\"10.1021/acsorginorgau.3c00062\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >In the present manuscript, we have developed a unique catalytic system by merging photoexcited ketone catalysis, halogen atom transfer (XAT), and nickel catalysis to forge C(sp<sup>3</sup>)–C(sp<sup>2</sup>) cross-electrophile coupling products from unactivated iodoalkanes and (hetero)aryl bromides. The synergistic catalytic system works under mild reaction conditions and tolerates a variety of functional groups; moreover, this strategy allows the late-stage modification of medicinally relevant molecules. Preliminary mechanistic studies reveal the role of the α-aminoalkyl radical, which further participates in the XAT process with alkyl iodides to generate the desired alkyl radical, which eventually intercepts with the nickel catalytic cycle to liberate the products in good to excellent yields.</p>\",\"PeriodicalId\":29797,\"journal\":{\"name\":\"ACS Organic & Inorganic Au\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2023-12-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00062\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Organic & Inorganic Au\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00062\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Organic & Inorganic Au","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00062","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synergistic Merger of Ketone, Halogen Atom Transfer (XAT), and Nickel-Mediated C(sp3)–C(sp2) Cross-Electrophile Coupling Enabled by Light
In the present manuscript, we have developed a unique catalytic system by merging photoexcited ketone catalysis, halogen atom transfer (XAT), and nickel catalysis to forge C(sp3)–C(sp2) cross-electrophile coupling products from unactivated iodoalkanes and (hetero)aryl bromides. The synergistic catalytic system works under mild reaction conditions and tolerates a variety of functional groups; moreover, this strategy allows the late-stage modification of medicinally relevant molecules. Preliminary mechanistic studies reveal the role of the α-aminoalkyl radical, which further participates in the XAT process with alkyl iodides to generate the desired alkyl radical, which eventually intercepts with the nickel catalytic cycle to liberate the products in good to excellent yields.
期刊介绍:
ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.