2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method: Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine

Jing Chen; Arthur Cammers-Goodwin

doi:10.1016/S0040-4039(02)02793-4

2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method: Ag₂O accelerates coupling over undesired ipso substitution (S_NAr) of fluorine

Jing Chen, Arthur Cammers-Goodwin

Chemistry

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

42 Scopus citations

Abstract

Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophilic substitution. Inclusion of Ag₂O accelerated coupling over ipso substitution.

Original language	English
Pages (from-to)	1503-1506
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4039(02)02793-4
State	Published - Feb 10 2003

Bibliographical note

Funding Information:
The authors thank the NSF (0111578) for financial support.

Funding

The authors thank the NSF (0111578) for financial support.

Funders	Funder number
National Science Foundation (NSF)	0111578

Keywords

Aryl cross coupling
Pd catalyst
Suzuki coupling
Transmetallation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(02)02793-4

Cite this

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title = "2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method: Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine",

abstract = "Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophilic substitution. Inclusion of Ag2O accelerated coupling over ipso substitution.",

keywords = "Aryl cross coupling, Pd catalyst, Suzuki coupling, Transmetallation",

author = "Jing Chen and Arthur Cammers-Goodwin",

note = "Funding Information: The authors thank the NSF (0111578) for financial support. ",

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language = "English",

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T1 - 2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method

T2 - Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine

AU - Chen, Jing

AU - Cammers-Goodwin, Arthur

N1 - Funding Information: The authors thank the NSF (0111578) for financial support.

PY - 2003/2/10

Y1 - 2003/2/10

N2 - Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophilic substitution. Inclusion of Ag2O accelerated coupling over ipso substitution.

AB - Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophilic substitution. Inclusion of Ag2O accelerated coupling over ipso substitution.

KW - Aryl cross coupling

KW - Pd catalyst

KW - Suzuki coupling

KW - Transmetallation

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