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Literature DB >> 30295492

Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment.

Osvaldo Gutierrez¹, Charles E Hendrick¹, Marisa C Kozlowski¹.

Abstract

Detailed computational (DFT) studies of the palladium(II)-catalyzed Claisen rearrangement of 2-allyloxy- and propargyloxyindoles revealed an unexpected divergent mode of reactivity. Subsequent experimental kinetic isotope effects are in accord with the mechanism derived from the computations. The computational results led to the development of Pd(II)-catalyzed [3,3]-sigmatropic rearrangement of 3-aryl substituted 2-propargylindoles.

Entities: Chemical Disease Gene Mutation

Year: 2018 PMID： 30295492 PMCID： PMC6201310 DOI： 10.1021/acs.orglett.8b02864

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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References

13 in total

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Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment.

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