An Efficient and General Method for Formylation of Aryl Bromides with CO2 and Poly(methylhydrosiloxane)

Bo Yu; Zhenzhen Yang; Yanfei Zhao; Leiduan Hao; Hongye Zhang; Xiang Gao; Buxing Han; Zhimin Liu

doi:10.1002/chem.201504320

An Efficient and General Method for Formylation of Aryl Bromides with CO₂ and Poly(methylhydrosiloxane)

Bo Yu, Zhenzhen Yang, Yanfei Zhao, Leiduan Hao, Hongye Zhang, Xiang Gao, Buxing Han, Zhimin Liu

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

57 Scopus citations

Abstract

The formylation of aryl halides with CO₂ to generate aryl aldehydes is challenging. Herein, we report a novel synthesis of aryl aldehydes by formylation of aryl bromides with CO₂ and a waste silane, poly(methylhydrosiloxane) (PMHS). It has been discovered that a simple combination of 1,3-bis(diphenyphosphino)propane (DPPP)-chelated Pd catalyst, Pd(DPPP)Cl₂, with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is able to effectively catalyze the reaction, leading to aryl aldehydes in moderate to excellent yields, and without any by-products in most cases. Moreover, this route could be extended to the formylation of aryl iodides with high efficiency. This approach is simple, less costly, and environmentally friendly, and also widens the applications of CO₂ to form value-added chemicals by the construction of new C-C bonds.

Original language	English
Pages (from-to)	1097-1102
Number of pages	6
Journal	Chemistry - A European Journal
Volume	22
Issue number	3
DOIs	https://doi.org/10.1002/chem.201504320
State	Published - Jan 18 2016
Externally published	Yes

Funding

The authors thank the National Natural Science Foundation of China for support of this work (grant nos. 21503239, 21125314, 21021003, 21373242).

Keywords

P ligands
aryl aldehydes
aryl bromides
carbon dioxide
formylation
green chemistry

Access to Document

10.1002/chem.201504320

Cite this

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title = "An Efficient and General Method for Formylation of Aryl Bromides with CO2 and Poly(methylhydrosiloxane)",

abstract = "The formylation of aryl halides with CO2 to generate aryl aldehydes is challenging. Herein, we report a novel synthesis of aryl aldehydes by formylation of aryl bromides with CO2 and a waste silane, poly(methylhydrosiloxane) (PMHS). It has been discovered that a simple combination of 1,3-bis(diphenyphosphino)propane (DPPP)-chelated Pd catalyst, Pd(DPPP)Cl2, with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is able to effectively catalyze the reaction, leading to aryl aldehydes in moderate to excellent yields, and without any by-products in most cases. Moreover, this route could be extended to the formylation of aryl iodides with high efficiency. This approach is simple, less costly, and environmentally friendly, and also widens the applications of CO2 to form value-added chemicals by the construction of new C-C bonds.",

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author = "Bo Yu and Zhenzhen Yang and Yanfei Zhao and Leiduan Hao and Hongye Zhang and Xiang Gao and Buxing Han and Zhimin Liu",

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AU - Yu, Bo

AU - Yang, Zhenzhen

AU - Zhao, Yanfei

AU - Hao, Leiduan

AU - Zhang, Hongye

AU - Gao, Xiang

AU - Han, Buxing

AU - Liu, Zhimin

PY - 2016/1/18

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N2 - The formylation of aryl halides with CO2 to generate aryl aldehydes is challenging. Herein, we report a novel synthesis of aryl aldehydes by formylation of aryl bromides with CO2 and a waste silane, poly(methylhydrosiloxane) (PMHS). It has been discovered that a simple combination of 1,3-bis(diphenyphosphino)propane (DPPP)-chelated Pd catalyst, Pd(DPPP)Cl2, with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is able to effectively catalyze the reaction, leading to aryl aldehydes in moderate to excellent yields, and without any by-products in most cases. Moreover, this route could be extended to the formylation of aryl iodides with high efficiency. This approach is simple, less costly, and environmentally friendly, and also widens the applications of CO2 to form value-added chemicals by the construction of new C-C bonds.

AB - The formylation of aryl halides with CO2 to generate aryl aldehydes is challenging. Herein, we report a novel synthesis of aryl aldehydes by formylation of aryl bromides with CO2 and a waste silane, poly(methylhydrosiloxane) (PMHS). It has been discovered that a simple combination of 1,3-bis(diphenyphosphino)propane (DPPP)-chelated Pd catalyst, Pd(DPPP)Cl2, with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is able to effectively catalyze the reaction, leading to aryl aldehydes in moderate to excellent yields, and without any by-products in most cases. Moreover, this route could be extended to the formylation of aryl iodides with high efficiency. This approach is simple, less costly, and environmentally friendly, and also widens the applications of CO2 to form value-added chemicals by the construction of new C-C bonds.

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