Intramolecular Catalyst Transfer over Sterically Hindered Arenes in Suzuki Cross-Coupling Reactions

Yu Xing Zhu; En Ci Li; Kang Shen; Xiaochun Hang; Peter V. Bonnesen; Kunlun Hong; Hong Hai Zhang; Wei Huang

doi:10.1002/ajoc.201900228

Intramolecular Catalyst Transfer over Sterically Hindered Arenes in Suzuki Cross-Coupling Reactions

Yu Xing Zhu, En Ci Li, Kang Shen, Xiaochun Hang, Peter V. Bonnesen, Kunlun Hong, Hong Hai Zhang, Wei Huang

Macromolecular Nanomaterials

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

6 Scopus citations

Abstract

The intramolecular catalyst transfer over sterically hindered arenes in Suzuki cross-coupling reaction was investigated by the reaction of ortho-substituted dibromoarenes with equimolar ortho-substituted phenylboronic acid in the presence of NHC based PEPPSI-IPr as catalyst. The diarylarene species of the form Ar’−Ar−Ar’ were observed as major product, which suggested the intramolecular transfer of Pd(0) over sterically hindered arenes proceeded smoothly in Suzuki cross-coupling reaction. Furthermore, our studies also demonstrated that intramolecular catalyst transfer could be a useful tool to improve the polymerization efficiency, especially in the synthesis of ortho-linked polyarenes.

Original language	English
Pages (from-to)	1506-1512
Number of pages	7
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	8
DOIs	https://doi.org/10.1002/ajoc.201900228
State	Published - Aug 2019

Funding

We thank the National Natural Science Foundation of China (Grant Numbers 21704041) for the support. Part of the syntheses was conducted at the Center for Nanophase Materials Sciences, which is a DOE Office of Science User Facility.

Funders	Funder number
Office of Science
National Natural Science Foundation of China	21704041

Keywords

Controlled Polymerization
Intramolecular Catalyst Transfer
Sterically Hindered Substrate

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10.1002/ajoc.201900228

Cite this

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abstract = "The intramolecular catalyst transfer over sterically hindered arenes in Suzuki cross-coupling reaction was investigated by the reaction of ortho-substituted dibromoarenes with equimolar ortho-substituted phenylboronic acid in the presence of NHC based PEPPSI-IPr as catalyst. The diarylarene species of the form Ar{\textquoteright}−Ar−Ar{\textquoteright} were observed as major product, which suggested the intramolecular transfer of Pd(0) over sterically hindered arenes proceeded smoothly in Suzuki cross-coupling reaction. Furthermore, our studies also demonstrated that intramolecular catalyst transfer could be a useful tool to improve the polymerization efficiency, especially in the synthesis of ortho-linked polyarenes.",

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AU - Shen, Kang

AU - Hang, Xiaochun

AU - Bonnesen, Peter V.

AU - Hong, Kunlun

AU - Zhang, Hong Hai

AU - Huang, Wei

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AB - The intramolecular catalyst transfer over sterically hindered arenes in Suzuki cross-coupling reaction was investigated by the reaction of ortho-substituted dibromoarenes with equimolar ortho-substituted phenylboronic acid in the presence of NHC based PEPPSI-IPr as catalyst. The diarylarene species of the form Ar’−Ar−Ar’ were observed as major product, which suggested the intramolecular transfer of Pd(0) over sterically hindered arenes proceeded smoothly in Suzuki cross-coupling reaction. Furthermore, our studies also demonstrated that intramolecular catalyst transfer could be a useful tool to improve the polymerization efficiency, especially in the synthesis of ortho-linked polyarenes.

KW - Controlled Polymerization

KW - Intramolecular Catalyst Transfer

KW - Sterically Hindered Substrate

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Intramolecular Catalyst Transfer over Sterically Hindered Arenes in Suzuki Cross-Coupling Reactions

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Keywords

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