文献类型：期刊文献

英文题名：Nickel-Catalyzed Carbonylative Negishi Cross-Coupling of Unactivated Secondary Alkyl Electrophiles with 1 atm CO Gas

作者：Zhang, Yetong[1,2];Cao, Qihang[1,2];Xi, Yang[1,2];Wu, Xianqing[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2,3]

机构：[1]East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Joint Int Res Lab Precis Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

年份：2024

卷号：146

期号：12

起止页码：7971

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20241215758333);WOS:【SCI-EXPANDED(收录号:WOS:001185152500001)，CCR-EXPANDED(收录号:WOS:001185152500001)】；

基金：This work was supported by the Key Project of Science and Technology Innovation 2030 (No. 2023ZD0121001, 2023ZD0121002), National Natural Science Foundation of China (22171079, 22371071, 92356301), Natural Science Foundation of Shanghai Municipality (21ZR1480400), Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (B16017), Scientific Committee of Shanghai (21JC1401700), the China Postdoctoral Science Foundation (2023TQ0118), Postdoctoral Fellowship Program of CPSF (GZB20230212), and the Fundamental Research Funds for the Central Universities. The authors thank the Analysis and Testing Center of East China University of Science and Technology for help with NMR and HRMS analysis.

语种：英文

外文关键词：Carbonylation - Ketones - Nickel compounds - Organometallics - Sulfur compounds

摘要：We describe a nickel-catalyzed carbonylative cross-coupling of unactivated secondary alkyl electrophiles with the organozinc reagent at atmospheric CO gas, thus allowing the expedient construction of unsymmetric dialkyl ketones with broad functional group tolerance. The leverage of a newly developed NN 2-pincer type ligand enables the chemoselective three-component carbonylation by overcoming the competing Negishi coupling, the undesired beta-hydride elimination, and dehalogenation of alkyl iodides side pathways. Both alkyl iodides and alkyl tosylates are compatible in the single electron transfer involved mechanism.