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Synfacts 2017; 13(10): 1076
DOI: 10.1055/s-0036-1591272
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Oxidative [1,2]-Brook Rearrangements via Hypervalent Silicon Intermediates

Contributor(s):
Paul Knochel
,
Dorothée Ziegler
Deng Y. Liu Q. Smith III AB. * University of Pennsylvania, Philadephia, USA
Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations.

J. Am. Chem. Soc. 2017;
139: 9487-9490
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Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Key words

Brook rearrangement - silicon - photoredox catalysis

Significance

The authors report an oxidative [1,2]-Brook rearrangement via hypervalent silicon species induced by single-electron transfer. The resulting reactive radicals could be employed either in conjugate additions to achieve formal alkylation or in radical couplings to achieve arylation.


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Comment

As shown in the control experiments, without light or a photocatalyst, almost all starting material remained. When no base was added to the reaction only a trace amount of the product was detected.


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