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Org Lett. 2012 Aug 17;14(16):4066-9. doi: 10.1021/ol301670d. Epub 2012 Jul 31.

Cascade carbopalladation reaction between alkynes and gem-dibromoolefins: facile access to monoannelated pentalenes.

Organic letters

Pablo Rivera-Fuentes, Margarete von Wantoch Rekowski, W Bernd Schweizer, Jean-Paul Gisselbrecht, Corinne Boudon, François Diederich

Affiliations

  1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich, Switzerland.

PMID: 22849571 DOI: 10.1021/ol301670d

Abstract

A carbopalladation cascade reaction of easily accessible gem-dibromoolefins and alkynes furnishes monobenzo- and mononaphthopentalenes. The new chromophores accessed by this short route exhibit small HOMO-LUMO gaps and redox amphoteric behavior with tunable redox potentials.

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