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. 2007 Aug 2;9(16):3073-5.
doi: 10.1021/ol071120f. Epub 2007 Jul 7.

Palladium-catalyzed synthesis of cyclopentane-fused benzocyclobutenes via tandem directed carbopalladation/C-H bond functionalization

Myra Beaudoin Bertrand  1 , John P Wolfe
Affiliations

Palladium-catalyzed synthesis of cyclopentane-fused benzocyclobutenes via tandem directed carbopalladation/C-H bond functionalization

Myra Beaudoin Bertrand et al. Org Lett. .

Abstract

A new Pd-catalyzed reaction for the stereoselective synthesis of cyclopentane-fused benzocyclobutenes is described. These transformations likely proceed via carbamate-directed carbopalladation followed by intramolecular C-H activation of an alkylpalladium intermediate. The mechanistic relationship between these transformations and Pd-catalyzed reactions of gamma-(n-Boc-amino)alkenes with aryl bromides that afford pyrrolidines is discussed. Differences in reactivity between Pd-amino and Pd-amido complexes appear to play a key role in the outcome of these transformations.

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Figures

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Side products
Scheme 1
Scheme 1
See this image and copyright information in PMC

References

    1. Ney JE, Wolfe JP. Angew Chem, Int Ed. 2004;43:3605. - PubMed
    2. Bertrand MB, Wolfe JP. Tetrahedron. 2005;61:6447.
    3. Ney JE, Wolfe JP. J Am Chem Soc. 2005;127:8644. - PMC - PubMed
    4. Bertrand MB, Wolfe JP. Org Lett. 2006;8:2353. - PMC - PubMed
    5. Wolfe JP. Eur J Org Chem. 2007:571. and references cited therein. - PMC - PubMed
    1. Bertrand MB, Leathen ML, Wolfe JP. Org Lett. 2007;9:457. - PMC - PubMed

    1. Dpe-Phos = bis(2-diphenylphosphinophenyl)ether.

    1. For Pd-catalyzed reactions of aryl bromides with norbornene and related bicyclo[2.2.n]alkenes that afford benzocyclobutene products, see: Catellani M, Chiusoli GP, Ricotti S. J Organomet Chem. 1985;296:C11.Catellani M, Chiusoli GP, Ricotti S, Sabini F. Gazz Chim Ital. 1985;115:685.Catellani M, Ferioli L. Synthesis. 1996:769.

    1. Sadana AK, Saini RK, Billups WE. Chem Rev. 2003;103:1539. - PubMed
    2. Mehta G, Kotha S. Tetrahedron. 2001;57:625.

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