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DOI: 10.1055/a-1681-4720
Base-Mediated Site-Selective Hydroamination of Alkenes
This research was supported by the Ministry of Education of Singapore Academic Research Fund Tier 1 [grant no. R-143-000-B57-114 (M.J.K.)]. We also thank the National University of Singapore for the continued support of our research program.
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-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1681-4720.
- Supporting Information
Publication History
Received: 20 September 2021
Accepted after revision: 28 October 2021
Accepted Manuscript online:
28 October 2021
Article published online:
14 December 2021
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