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The synthesis of functionalized azepenes and piperidines bearing an α-cycloheptenone or benzotropone derivative has been accomplished through direct reductive cross-coupling of α-bromo eneformamides or enecarbamates with highly versatile α-bromo benzotropone derivatives, under cobalt catalysis. The coupling products have been further elaborated to other synthetically useful aza-heterocyclic frameworks.

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The regioselective synthesis of α,β-difunctionalized (alkenyl, aryl, sulfonyl, allyl, or alkynyl) azepenes has been accomplished through α-halo eneformamides. A successful implementation of the vicinal functionalization strategy has led to a one-pot synthesis of 2-benzazepanes whose benzenoid portion is highly functionalized.

Direct Access to Functionalized Benzotropones, Azepanes, and Piperidines by Reductive Cross-Coupling of -Bromo Enones with -Bromo Enamides. -[under cobalt catalysis]. -(BENG*, T. K.; SINCAVAGE, K.; SILAIRE, A. W. V.; ALWALI, A.; BASSLER, D. P.; SPENCE, L. E.; BEALE, O.; Org. Biomol. Chem. 13 (2015) 19, 5349-5353, http://dx.