Radical C-H Arylation of Oxazoles with Aryl Iodides: Dppf as an Electron-Transfer Mediator for Cs2CO3

Zhengwei Guo; Man Li; Xue Qing Mou; Gang He; Xiao Song Xue; Gong Chen

doi:10.1021/acs.orglett.8b00530

Radical C-H Arylation of Oxazoles with Aryl Iodides: Dppf as an Electron-Transfer Mediator for Cs₂CO₃

Zhengwei Guo, Man Li, Xue Qing Mou, Gang He, Xiao Song Xue, Gong Chen

Chemistry

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

32 Scopus citations

Abstract

A radical C-H arylation reaction of oxazoles with (hetero)aryl iodides using Cs₂CO₃ as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO₃^-, enhancing its SET reducing ability to generate an aryl radical from ArI.

Original language	English (US)
Pages (from-to)	1684-1687
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.8b00530
State	Published - Mar 16 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00530

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title = "Radical C-H Arylation of Oxazoles with Aryl Iodides: Dppf as an Electron-Transfer Mediator for Cs2CO3",

abstract = "A radical C-H arylation reaction of oxazoles with (hetero)aryl iodides using Cs2CO3 as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO3-, enhancing its SET reducing ability to generate an aryl radical from ArI.",

author = "Zhengwei Guo and Man Li and Mou, {Xue Qing} and Gang He and Xue, {Xiao Song} and Gong Chen",

note = "Funding Information: We gratefully thank the National Natural Science Foundation of China (21421062, 21502098, 21672105, 21772098) for financial support of this work. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b00530",

language = "English (US)",

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T1 - Radical C-H Arylation of Oxazoles with Aryl Iodides

T2 - Dppf as an Electron-Transfer Mediator for Cs2CO3

AU - Guo, Zhengwei

AU - Li, Man

AU - Mou, Xue Qing

AU - He, Gang

AU - Xue, Xiao Song

AU - Chen, Gong

N1 - Funding Information: We gratefully thank the National Natural Science Foundation of China (21421062, 21502098, 21672105, 21772098) for financial support of this work. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/3/16

Y1 - 2018/3/16

N2 - A radical C-H arylation reaction of oxazoles with (hetero)aryl iodides using Cs2CO3 as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO3-, enhancing its SET reducing ability to generate an aryl radical from ArI.

AB - A radical C-H arylation reaction of oxazoles with (hetero)aryl iodides using Cs2CO3 as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO3-, enhancing its SET reducing ability to generate an aryl radical from ArI.

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Radical C-H Arylation of Oxazoles with Aryl Iodides: Dppf as an Electron-Transfer Mediator for Cs₂CO₃

Abstract

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