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

Min Cao; Ahmet Yesilcimen; Soumil Prasad; Jason Genova; Tanner Myers; Masayuki Wasa

doi:10.1039/D0OB01678K

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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†

Min Cao,^a Ahmet Yesilcimen,^a Soumil Prasad,^a Jason Genova,^a Tanner Myers^a and Masayuki Wasa

*^a

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* Corresponding authors

^a Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA
E-mail: wasa@bc.edu

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.

This article is part of the themed collections: Hybrid Catalysis and Catalysis & biocatalysis in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB01678K
Article type: Communication
Submitted: 13 avq 2020
Accepted: 07 sen 2020
First published: 07 sen 2020

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

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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

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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Organic & Biomolecular Chemistry