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. 2011 Mar 4;13(5):1076-9.
doi: 10.1021/ol103121r. Epub 2011 Feb 3.

Palladium-catalyzed 1,1-aryloxygenation of terminal olefins

Andrew D Satterfield  1 , Asako Kubota, Melanie S Sanford
Affiliations

Palladium-catalyzed 1,1-aryloxygenation of terminal olefins

Andrew D Satterfield et al. Org Lett. .

Abstract

This paper describes the 1,1-arylacetoxylation of diverse α-olefins using organostannanes and hypervalent iodine oxidants. The reaction provides a convergent approach for generating a C-C and a C-O bond as well as a new stereocenter in a single catalytic transformation.

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Figures

Scheme 1
Scheme 1
Oxidatively Intecepting Heck Intermediates
Scheme 2
Scheme 2
1,2-Arylacetoxylation with p-Methoxystyrene
Scheme 3
Scheme 3
1,2-Arylacetoxylation with Vinyl Ether Substrates Yields determined by 1H NMR spectroscopic analysis of crude reaction mixtures; isolated yields were significantly lower due to decomposition of the mixed acetal products on silica gel. See Supporting Information for full details.
Scheme 4
Scheme 4
1,4-Arylacetoxylation of 2,3-Dihydrofuran
Scheme 5
Scheme 5
1,1-Phenylacetoxylation via Benzene C-H Activation
See this image and copyright information in PMC

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