Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols

Seath, Ciaran P. and Wilson, Kirsty L. and Campbell, Angus and Mowat, Jenna M. and Watson, Allan J. B. (2016) Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols. Chemical Communications (56). pp. 8703-8706. ISSN 1359-7345

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    Abstract

    A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(I)/Pd(0)/Cu(II) catalysis. 2-Iodoanilines and phenols undergo a Cu(I)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(II)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.

    ORCID iDs

    Seath, Ciaran P. ORCID logoORCID: https://orcid.org/0000-0002-6774-128X, Wilson, Kirsty L. ORCID logoORCID: https://orcid.org/0000-0002-4382-6246, Campbell, Angus, Mowat, Jenna M. and Watson, Allan J. B.;