Issue 9, 2014

A sidearm-assisted phosphine for catalytic ylide intramolecular cyclopropanation

Abstract

The first phosphine-catalyzed cyclopropanation reaction via covalent ylide catalysis has been realized with high efficiency in the presence of sidearm-assisted phosphine catalysts. An ether sidearm group is found critical to turn on the catalytic activity. Crystal structures of the catalyst-derived phosphonium salts indicated a significant O⋯P+ interaction between the pendant ether oxygen and the phosphonium center, which is believed to favor the catalyst regeneration. DFT calculations rationalize the insight of the sidearm effects.

Graphical abstract: A sidearm-assisted phosphine for catalytic ylide intramolecular cyclopropanation

Supplementary files

Article information

Article type
Research Article
Submitted
20 aug 2014
Accepted
30 aug 2014
First published
10 sep 2014

Org. Chem. Front., 2014,1, 1035-1039

A sidearm-assisted phosphine for catalytic ylide intramolecular cyclopropanation

J. Zhu, H. Chen, S. Liao, Y. Li and Y. Tang, Org. Chem. Front., 2014, 1, 1035 DOI: 10.1039/C4QO00232F

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