Issue 36, 2020

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

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 Brønsted 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

Supplementary files

Article information

Article type
Communication
Submitted
13 avq 2020
Accepted
07 sen 2020
First published
07 sen 2020

Org. Biomol. Chem., 2020,18, 7090-7093

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

M. Cao, A. Yesilcimen, S. Prasad, J. Genova, T. Myers and M. Wasa, Org. Biomol. Chem., 2020, 18, 7090 DOI: 10.1039/D0OB01678K

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