Sequential Conia-ene-type cyclization and Negishi coupling by cooperative functions of B(C6F5)3, ZnI2, Pd(PPh3)4 and an amine?

Organic & Biomolecular Chemistry Pub Date: 2020-09-07 DOI: 10.1039/D0OB01678K

Abstract

We disclose a method for sequential Conia-ene-type cyclization/Negishi coupling for the union of alkynyl ketones and aryl iodides. This process is promoted through cooperative actions of Lewis acidic B(C6F5)3, ZnI2, Pd-based complex, and a Br?nsted basic amine. The three Lewis acid catalysts with potential overlapping functions play their independent roles as activators of carbonyl group, alkyne moiety, and alkenyl zinc intermediate, respectively. A variety of 1,2,3-substituted cyclopentenes can be synthesized with high efficiency.

Graphical abstract: Sequential Conia-ene-type cyclization and Negishi coupling by cooperative functions of B(C6F5)3, ZnI2, Pd(PPh3)4 and an amine
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