Nickel-Catalyzed Chemo-, Regio- and Diastereoselective Bond Formation through Proximal C-C Cleavage of Benzocyclobutenones

Francisco Juliá-Hernández; Asraa Ziadi; Akira Nishimura; Ruben Martin

doi:10.1002/anie.201503461

Nickel-Catalyzed Chemo-, Regio- and Diastereoselective Bond Formation through Proximal C-C Cleavage of Benzocyclobutenones

Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9537-41. doi: 10.1002/anie.201503461. Epub 2015 Jun 11.

Authors

Francisco Juliá-Hernández¹, Asraa Ziadi¹, Akira Nishimura¹, Ruben Martin^{2

3}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).
² Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain). rmartinromo@iciq.es.
³ Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluïs Companys, 23, 08010 Barcelona (Spain). rmartinromo@iciq.es.

PMID: 26096718
DOI: 10.1002/anie.201503461

Abstract

The first catalytic intermolecular proximal C1-C2 cleavage of benzocyclobutenones (BCB) without prior carbonyl activation or employing noble metals has been developed. This protocol operates at room temperature and is characterized by an exquisite chemo-, regio- and diastereoselectivity profile, constituting a unique platform for preparing an array of elusive carbocyclic skeletons.

Keywords: CC activation; benzocyclobutenones; nickel catalysis; ring strain.