Iridium-Catalyzed Remote Site-Switchable Hydroarylation of Alkenes Controlled by Ligands

被引:0
|
作者
Li, Fei [1 ]
Luo, Yicong [1 ]
Ren, Jinbao [1 ]
Yuan, Qianjia [1 ]
Yan, Deyue [1 ]
Zhang, Wanbin [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Frontiers Sci Ctr Transformat Mol, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkene Mixtures; Chain-Walking; Iridium; Regioconvergence; Site-Selectivity;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iridium-catalyzed remote site-switchable hydroarylation of alkenes was reported, delivering the products functionalized at the subterminal methylene and terminal methyl positions on an alkyl chain controlled by two different ligands, respectively, in good yields and with good to excellent site-selectivities. The catalytic system showed good functional group tolerance and a broad substrate scope, including unactivated and activated alkenes. More importantly, the regioconvergent transformations of mixtures of isomeric alkenes were also successfully realized. The results of the mechanistic studies demonstrate that the reaction undergoes a chain-walking process to give an [Ar-Ir-H] complex of terminal alkene. The subsequent processes proceed through the modified Chalk-Harrod-type mechanism via the migratory insertion of terminal alkene into the Ir-C bond followed by C-H reductive elimination to afford the hydrofunctionalization products site-selectively.
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页数:13
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