Cu(OTf)2-mediated fluorination of aryltrifluoroborates with potassium fluoride

Yingda Ye; Sydonie D. Schimler; Patrick S. Hanley; Melanie S. Sanford

doi:10.1021/ja408607r

Cu(OTf)₂-mediated fluorination of aryltrifluoroborates with potassium fluoride

Yingda Ye
, Sydonie D. Schimler
, Patrick S. Hanley
, Melanie S. Sanford

Chemistry (Twin Cities)

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

186 Scopus citations

Abstract

This Communication describes the Cu(OTf)₂-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1) as a mediator for the aryl-F coupling and (2) as an oxidant for accessing a proposed Cu^III(aryl)(F) intermediate.

Original language	English (US)
Pages (from-to)	16292-16295
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	44
DOIs	https://doi.org/10.1021/ja408607r
State	Published - Nov 6 2013

Publisher link

10.1021/ja408607r

Find It

Find It at U of M Libraries

Cite this

@article{4cba9da2fbff441699fd245e6bb83d98,

title = "Cu(OTf)2-mediated fluorination of aryltrifluoroborates with potassium fluoride",

abstract = "This Communication describes the Cu(OTf)2-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1) as a mediator for the aryl-F coupling and (2) as an oxidant for accessing a proposed CuIII(aryl)(F) intermediate.",

author = "Yingda Ye and Schimler, \{Sydonie D.\} and Hanley, \{Patrick S.\} and Sanford, \{Melanie S.\}",

year = "2013",

month = nov,

day = "6",

doi = "10.1021/ja408607r",

language = "English (US)",

volume = "135",

pages = "16292--16295",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "44",

}

TY - JOUR

T1 - Cu(OTf)2-mediated fluorination of aryltrifluoroborates with potassium fluoride

AU - Ye, Yingda

AU - Schimler, Sydonie D.

AU - Hanley, Patrick S.

AU - Sanford, Melanie S.

PY - 2013/11/6

Y1 - 2013/11/6

N2 - This Communication describes the Cu(OTf)2-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1) as a mediator for the aryl-F coupling and (2) as an oxidant for accessing a proposed CuIII(aryl)(F) intermediate.

AB - This Communication describes the Cu(OTf)2-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1) as a mediator for the aryl-F coupling and (2) as an oxidant for accessing a proposed CuIII(aryl)(F) intermediate.

UR - https://www.scopus.com/pages/publications/84887657120

UR - https://www.scopus.com/pages/publications/84887657120#tab=citedBy

U2 - 10.1021/ja408607r

DO - 10.1021/ja408607r

M3 - Article

C2 - 24160267

AN - SCOPUS:84887657120

SN - 0002-7863

VL - 135

SP - 16292

EP - 16295

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

Cu(OTf)₂-mediated fluorination of aryltrifluoroborates with potassium fluoride

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this