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Issue 11, 2017
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Photoredox meets gold Lewis acid catalysis in the alkylative semipinacol rearrangement: a photocatalyst with a dark side

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Abstract

The alkylative semipinacol rearrangement of a variety of TMS protected α-styrenyl substituted cyclic alcohols with unactivated bromoalkanes that merge photoredox and Au(I)/Au(III) catalysis has been achieved. This redox neutral rearrangement is marked by a dimeric Au(I) photocatalyst that plays two roles; photoredox activation of bromoalkanes and Au(III)-mediated semipinacol rearrangement coupled with C(sp3)–C(sp3) reductive elimination; a reaction mode rarely accessed. This operationally simple methodology contains readily available starting materials that undergo reaction with [Au2(dppm)2]Cl2 upon irradiation with UVA LEDs, furnishing diversified ketone products. Primary, secondary, and tertiary bromoalkanes and a range of TMS protected α-styrenyl substituted alcohols were investigated in this transformation.

Graphical abstract: Photoredox meets gold Lewis acid catalysis in the alkylative semipinacol rearrangement: a photocatalyst with a dark side

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Article information


Submitted
16 Jul 2017
Accepted
31 Jul 2017
First published
01 Aug 2017

Org. Chem. Front., 2017,4, 2092-2096
Article type
Research Article

Photoredox meets gold Lewis acid catalysis in the alkylative semipinacol rearrangement: a photocatalyst with a dark side

M. Zidan, T. McCallum, L. Thai-Savard and L. Barriault, Org. Chem. Front., 2017, 4, 2092
DOI: 10.1039/C7QO00590C

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