Base-Mediated Site-Selective Hydroamination of Alkenes

Ping Li; Boon Chong Lee; Xiaoxiang Zhang; Ming Joo Koh

doi:10.1055/a-1681-4720

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(06): 1566-1576
DOI: 10.1055/a-1681-4720

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Base-Mediated Site-Selective Hydroamination of Alkenes

Ping Li‡

^aHenan Key Lab of Cable Structure and Materials, College of Cable Engineering, Henan Institute of Technology, Xinxiang, 453003, P. R. of China

^bCo-Innovation Center for Efficient Processing and Utilization of Forest Products, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P. R. of China

^cDepartment of Chemistry, National University of Singapore, 4 Science Drive 2, 117544, Singapore

,

Boon Chong Lee‡

^cDepartment of Chemistry, National University of Singapore, 4 Science Drive 2, 117544, Singapore

,

Xiaoxiang Zhang

^bCo-Innovation Center for Efficient Processing and Utilization of Forest Products, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P. R. of China

,

Ming Joo Koh ∗

^cDepartment of Chemistry, National University of Singapore, 4 Science Drive 2, 117544, Singapore

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Abstract

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Abstract

We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tert-butoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access β-arylamines from terminal aliphatic alkenes.

Key words

hydroamination - remote alkene functionalization - base-mediated - regioselectivity - transition-metal-free

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Referenzen

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