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. 2013 Oct 4;15(19):5008-11.
doi: 10.1021/ol4023358. Epub 2013 Sep 18.

Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates

Vaneet Saini  1 , Longyan Liao, Qiaofeng Wang, Ranjan Jana, Matthew S Sigman
Affiliations

Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates

Vaneet Saini et al. Org Lett. .

Abstract

An efficient protocol for the one-step synthesis of biologically relevant 1,1-diarylalkanes has been described. This reaction introduces two different aryl groups across the terminal end of simple feedstock alkenes such as ethylene and allylic carbonates. The propensity to generate π-benzylpalladium intermediates dictates the exclusive 1,1-regioselectivity observed in the product.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Scope of the 1,1-diarylation of ethylene.
Figure 2
Figure 2
Scope of 1,1-diarylation of allyl phenyl carbonate.
Figure 3
Figure 3
Scope of 1,1-diarylation of various alkenes.
Scheme 1
Scheme 1
Proposed 1,1-Difunctionalization of Ethylene/Terminal Olefins with Aryldiazonium Salts and Boronic Acids
See this image and copyright information in PMC

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