Issue 6, 2019

Selective carbonylation of benzene to benzaldehyde using a phosphorus–nitrogen PN3P–rhodium(i) complex

Abstract

A PN3P pincer ligand (1) bearing dicyclopentylphosphine substituents reacts with [Rh(COD)Cl]2 (COD = 1,5-cyclooctadiene) to produce the complex (PN3P)RhCl (2). Treatment of a benzene solution of 2 with KN(SiMe3)2 stimulates a dearomatization process, and C–H activation of benzene is achieved through the rearomatization of the central pyridine ring. This deprotonation/reprotonation of the NH arm of 2 gives the phenyl complex (PN3P)Rh(C6H5) (3). The subsequent introduction of CO gas into 3 yields the benzoyl complex (PN3P)RhCO (C6H5) (4), which can release benzaldehyde upon treatment with diluted HCl solution and regenerates 2.

Graphical abstract: Selective carbonylation of benzene to benzaldehyde using a phosphorus–nitrogen PN3P–rhodium(i) complex

Supplementary files

Article information

Article type
Research Article
Submitted
18 8月 2018
Accepted
07 11月 2018
First published
07 11月 2018

Org. Chem. Front., 2019,6, 721-724

Selective carbonylation of benzene to benzaldehyde using a phosphorus–nitrogen PN3P–rhodium(I) complex

C. Zhou, J. Hu, Y. Wang, C. Yao, P. Chakraborty, H. Li, C. Guan, M. Huang and K. Huang, Org. Chem. Front., 2019, 6, 721 DOI: 10.1039/C8QO00892B

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements