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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Author affiliations

* 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

Download options Please wait...

Supplementary files

Supplementary information PDF (2399K)

Article information

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

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry