Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C−H activation

Dingyi Wang, Ben Dong, Yandong Wang, Jiasheng Qian, Jinjun Zhu, Yue Zhao and Zhuangzhi Shi ()
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Dingyi Wang: Nanjing University
Ben Dong: Nanjing University
Yandong Wang: Nanjing University
Jiasheng Qian: Nanjing University
Jinjun Zhu: Nanjing University
Yue Zhao: Nanjing University
Zhuangzhi Shi: Nanjing University

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Biarylphosphines have been widely applied as ligands in various synthetic methods, especially in transition-metal-catalysed carbon-carbon and carbon-heteroatom bond cross-coupling reactions. Based on the outstanding properties of the parent scaffolds, a general method for in situ modification of the commercial tertiary phosphine ligands to access a series of ligands is in high demand. Here we show that a rhodium-catalysed system is introduced for the hydroarylation of alkenes and alkynes with tertiary phosphines through P(III)-chelation assisted C-H activation. A series of ligand libraries containing alkyl and alkenyl substituted groups with different steric and electronic properties are obtained in high yields. Furthermore, several experimental studies are performed to uncover the key mechanistic features of the linear-selective hydroarylation of alkenes and branch-selective hydroarylation of alkynes.

Date: 2019
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DOI: 10.1038/s41467-019-11420-5

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