Rhodium-Catalyzed Formylation of Aryl Halides with CO2 and H2

Zhenghui Liu; Zhenzhen Yang; Bo Yu; Xiaoxiao Yu; Hongye Zhang; Yanfei Zhao; Peng Yang; Zhimin Liu

doi:10.1021/acs.orglett.8b02027

Rhodium-Catalyzed Formylation of Aryl Halides with CO₂ and H₂

Zhenghui Liu, Zhenzhen Yang, Bo Yu, Xiaoxiao Yu, Hongye Zhang, Yanfei Zhao, Peng Yang, Zhimin Liu

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

Abstract

The reductive formylation of aryl iodides/bromides to aryl aldehydes using CO₂/H₂ is presented for the first time. It was realized over a catalytic system composed of RhI₃ or RhI₃/Pd(dppp)Cl₂ (dppp = 1,3-bis(diphenyphosphino)propane) and PPh₃ in the presence of Ac₂O/Et₃N at 100 °C, affording aromatic aldehydes in good to excellent yields, together with good functional-group tolerance and broad substrate scope. The reaction proceeds through three cascade steps, involving HCOOH formation, CO release, and formylation of aryl halides.

Original language	English
Pages (from-to)	5130-5134
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.8b02027
State	Published - Sep 7 2018
Externally published	Yes

Funding

We thank the National Natural Science Foundation of China (Nos. 21673256 and 21533011) and the Chinese Academy of Sciences (QYZDY-SSW-SLH013-2).

Funders	Funder number
National Natural Science Foundation of China	21673256, 21533011
Chinese Academy of Sciences	QYZDY-SSW-SLH013-2

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title = "Rhodium-Catalyzed Formylation of Aryl Halides with CO2 and H2 ",

abstract = "The reductive formylation of aryl iodides/bromides to aryl aldehydes using CO2/H2 is presented for the first time. It was realized over a catalytic system composed of RhI3 or RhI3/Pd(dppp)Cl2 (dppp = 1,3-bis(diphenyphosphino)propane) and PPh3 in the presence of Ac2O/Et3N at 100 °C, affording aromatic aldehydes in good to excellent yields, together with good functional-group tolerance and broad substrate scope. The reaction proceeds through three cascade steps, involving HCOOH formation, CO release, and formylation of aryl halides.",

author = "Zhenghui Liu and Zhenzhen Yang and Bo Yu and Xiaoxiao Yu and Hongye Zhang and Yanfei Zhao and Peng Yang and Zhimin Liu",

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T1 - Rhodium-Catalyzed Formylation of Aryl Halides with CO2 and H2

AU - Liu, Zhenghui

AU - Yang, Zhenzhen

AU - Yu, Bo

AU - Yu, Xiaoxiao

AU - Zhang, Hongye

AU - Zhao, Yanfei

AU - Yang, Peng

AU - Liu, Zhimin

PY - 2018/9/7

Y1 - 2018/9/7

N2 - The reductive formylation of aryl iodides/bromides to aryl aldehydes using CO2/H2 is presented for the first time. It was realized over a catalytic system composed of RhI3 or RhI3/Pd(dppp)Cl2 (dppp = 1,3-bis(diphenyphosphino)propane) and PPh3 in the presence of Ac2O/Et3N at 100 °C, affording aromatic aldehydes in good to excellent yields, together with good functional-group tolerance and broad substrate scope. The reaction proceeds through three cascade steps, involving HCOOH formation, CO release, and formylation of aryl halides.

AB - The reductive formylation of aryl iodides/bromides to aryl aldehydes using CO2/H2 is presented for the first time. It was realized over a catalytic system composed of RhI3 or RhI3/Pd(dppp)Cl2 (dppp = 1,3-bis(diphenyphosphino)propane) and PPh3 in the presence of Ac2O/Et3N at 100 °C, affording aromatic aldehydes in good to excellent yields, together with good functional-group tolerance and broad substrate scope. The reaction proceeds through three cascade steps, involving HCOOH formation, CO release, and formylation of aryl halides.

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DO - 10.1021/acs.orglett.8b02027

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JO - Organic Letters

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ER -

Rhodium-Catalyzed Formylation of Aryl Halides with CO₂ and H₂

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