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. 2010 Aug 16;49(35):6169-73.
doi: 10.1002/anie.201002077.

Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination

Keary M Engle  1 , Dong-Hui Wang, Jin-Quan Yu
Affiliations

Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination

Keary M Engle et al. Angew Chem Int Ed Engl. .

Abstract

Complementary catalytic systems have been developed in which the reactivity/selectivity balance in Pd(II)-catalyzed ortho-C–H olefination can be modulated through ligand control. This allows for sequential C–H functionalization for the rapid preparation of 1,2,3-trisubstituted arenes. Additionally, a rare example of iterative C–H activation, in which a newly installed functional group directs subsequent C–H activation has been demonstrated.

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Figures

Scheme 1
Scheme 1
Sequential directed C–H functionalization.
Scheme 2
Scheme 2
The challenges of sequential directed C–H functionalization.
Scheme 3
Scheme 3
Outline of this work.
Scheme 4
Scheme 4
Sequential and iterative C–H olefination to synthesize multiply substituted arenes. (See Supporting Information for experimental details.)
See this image and copyright information in PMC

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