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Issue 36, 2020
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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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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

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Article information


Submitted
13 Aug 2020
Accepted
07 Sep 2020
First published
07 Sep 2020

Org. Biomol. Chem., 2020,18, 7090-7093
Article type
Communication

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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