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

Chunhui Zhou, Jinsong Hu, Yuan Wang, Changguang Yao, Priyanka Chakraborty, Huaifeng Li, Chao Guan, Mei-Hui Huang, Kuo-Wei Huang

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)721-724
Number of pages4
JournalOrganic Chemistry Frontiers
Volume6
Issue number6
DOIs
StatePublished - 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial support from the King Abdullah University of Science and Technology (KAUST) is acknowledged. This work was dedicated to Professor Xiyan Lu on the occasion of his 90th birthday.

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