Hydroarylation of Alkenes by Protonation/Friedel−Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters

Jordi Bures; Christian D.-T. Nielsen; Andrew J P White; David Sale; Alan C. Spivey

doi:10.1021/acs.joc.9b02393

Hydroarylation of Alkenes by Protonation/Friedel−Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters

Jordi Bures, Christian D.-T. Nielsen, Andrew J P White, David Sale, Alan C. Spivey

Organic Chemistry Group

Research output: Contribution to journal › Article › peer-review

Abstract

Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Brønsted bases and
protonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel−Crafts
hydroarylation which proceeds with Markovnikov selectivity and is orthogonal to traditional metal-catalyzed processes.
Intermolecular transfer hydrogenation and hydrothiolation under analogous conditions are also demonstrated.

Original language	English
Pages (from-to)	14965
Number of pages	14973
Journal	The Journal of organic chemistry
Early online date	21 Oct 2019
DOIs	https://doi.org/10.1021/acs.joc.9b02393
Publication status	Published - 15 Nov 2019

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abstract = "Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Br{\o}nsted bases andprotonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel−Craftshydroarylation which proceeds with Markovnikov selectivity and is orthogonal to traditional metal-catalyzed processes.Intermolecular transfer hydrogenation and hydrothiolation under analogous conditions are also demonstrated.",

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AU - White, Andrew J P

AU - Sale, David

AU - Spivey, Alan C.

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N2 - Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Brønsted bases andprotonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel−Craftshydroarylation which proceeds with Markovnikov selectivity and is orthogonal to traditional metal-catalyzed processes.Intermolecular transfer hydrogenation and hydrothiolation under analogous conditions are also demonstrated.

AB - Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Brønsted bases andprotonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel−Craftshydroarylation which proceeds with Markovnikov selectivity and is orthogonal to traditional metal-catalyzed processes.Intermolecular transfer hydrogenation and hydrothiolation under analogous conditions are also demonstrated.

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ER -

Hydroarylation of Alkenes by Protonation/Friedel−Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters

Abstract

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