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Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

The reductive carbonylation of aryl iodides to aryl aldehydes possesses broad application prospects. We present an efficient and facile Rh-based catalytic system composed of the commercially available Rh salt RhCl(3)·3H(2)O, PPh(3) as phosphine ligand, and Et(3)N as the base, for the synthesis of ar...

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Autores principales: Liu, Zhenghui, Wang, Peng, Yan, Zhenzhong, Chen, Suqing, Yu, Dongkun, Zhao, Xinhui, Mu, Tiancheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155901/
https://www.ncbi.nlm.nih.gov/pubmed/32318121
http://dx.doi.org/10.3762/bjoc.16.61
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author Liu, Zhenghui
Wang, Peng
Yan, Zhenzhong
Chen, Suqing
Yu, Dongkun
Zhao, Xinhui
Mu, Tiancheng
author_facet Liu, Zhenghui
Wang, Peng
Yan, Zhenzhong
Chen, Suqing
Yu, Dongkun
Zhao, Xinhui
Mu, Tiancheng
author_sort Liu, Zhenghui
collection PubMed
description The reductive carbonylation of aryl iodides to aryl aldehydes possesses broad application prospects. We present an efficient and facile Rh-based catalytic system composed of the commercially available Rh salt RhCl(3)·3H(2)O, PPh(3) as phosphine ligand, and Et(3)N as the base, for the synthesis of arylaldehydes via the reductive carbonylation of aryl iodides with CO and H(2) under relatively mild conditions with a broad substrate range affording the products in good to excellent yields. Systematic investigations were carried out to study the experimental parameters. We explored the optimal ratio of Rh salt and PPh(3) ligand, substrate scope, carbonyl source and hydrogen source, and the reaction mechanism. Particularly, a scaled-up experiment indicated that the catalytic method could find valuable applications in industrial productions. The low gas pressure, cheap ligand and low metal dosage could significantly improve the practicability in both chemical researches and industrial applications.
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spelling pubmed-71559012020-04-21 Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas Liu, Zhenghui Wang, Peng Yan, Zhenzhong Chen, Suqing Yu, Dongkun Zhao, Xinhui Mu, Tiancheng Beilstein J Org Chem Full Research Paper The reductive carbonylation of aryl iodides to aryl aldehydes possesses broad application prospects. We present an efficient and facile Rh-based catalytic system composed of the commercially available Rh salt RhCl(3)·3H(2)O, PPh(3) as phosphine ligand, and Et(3)N as the base, for the synthesis of arylaldehydes via the reductive carbonylation of aryl iodides with CO and H(2) under relatively mild conditions with a broad substrate range affording the products in good to excellent yields. Systematic investigations were carried out to study the experimental parameters. We explored the optimal ratio of Rh salt and PPh(3) ligand, substrate scope, carbonyl source and hydrogen source, and the reaction mechanism. Particularly, a scaled-up experiment indicated that the catalytic method could find valuable applications in industrial productions. The low gas pressure, cheap ligand and low metal dosage could significantly improve the practicability in both chemical researches and industrial applications. Beilstein-Institut 2020-04-08 /pmc/articles/PMC7155901/ /pubmed/32318121 http://dx.doi.org/10.3762/bjoc.16.61 Text en Copyright © 2020, Liu et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Liu, Zhenghui
Wang, Peng
Yan, Zhenzhong
Chen, Suqing
Yu, Dongkun
Zhao, Xinhui
Mu, Tiancheng
Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
title Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
title_full Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
title_fullStr Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
title_full_unstemmed Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
title_short Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
title_sort rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155901/
https://www.ncbi.nlm.nih.gov/pubmed/32318121
http://dx.doi.org/10.3762/bjoc.16.61
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