A Convenient Photocatalytic Fluorination of Unactivated CH Bonds

Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site‐selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination...

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Bibliographic Details
Published in	Angewandte Chemie International Edition Vol. 53; no. 18; pp. 4690 - 4693
Main Authors	Halperin, Shira D., Fan, Hope, Chang, Stanley, Martin, Rainer E., Britton, Robert
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 25.04.2014 WILEY‐VCH Verlag Wiley
Subjects	Amino acids Blocking Carbon - chemistry Catalysis Chemistry Chemistry, Multidisciplinary CH activation Derivatives Economics Fluorides Fluorination Fluorine - chemistry Fluorine Radioisotopes - chemistry Halogenation Hydrogen - chemistry Light Natural products Photocatalysis photochemistry Physical Sciences polyoxometalates Positron-Emission Tomography Science & Technology Sulfonamides - chemistry Tomography tungsten EXCITED-STATE ACIDS amino acids REACTIVITY ALDEHYDES MEDICINAL CHEMISTRY ALKENES CH activation tungsten photochemistry polyoxometalates RADICALS PET ALKANES CH activation
Online Access	Get full text
ISSN	1433-7851 1521-3773 1521-3773
DOI	10.1002/anie.201400420

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Abstract	Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site‐selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen ing ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N‐fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. The direct fluorination of unactivated C(sp3)H bonds is catalyzed by the inexpensive photocatalyst tetrabutylammonium decatungstate (TBADT). This convenient reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acids.
AbstractList	Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives.Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site‐selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N ‐fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated C--H bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated C--H bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. The direct fluorination of unactivated C(sp super(3))--H bonds is catalyzed by the inexpensive photocatalyst tetrabutylammonium decatungstate (TBADT). This convenient reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acids. Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site‐selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen ing ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N‐fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives. The direct fluorination of unactivated C(sp3)H bonds is catalyzed by the inexpensive photocatalyst tetrabutylammonium decatungstate (TBADT). This convenient reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acids.
Author	Chang, Stanley Fan, Hope Britton, Robert Halperin, Shira D. Martin, Rainer E.
Author_xml	– sequence: 1 givenname: Shira D. surname: Halperin fullname: Halperin, Shira D. organization: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada) – sequence: 2 givenname: Hope surname: Fan fullname: Fan, Hope organization: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada) – sequence: 3 givenname: Stanley surname: Chang fullname: Chang, Stanley organization: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada) – sequence: 4 givenname: Rainer E. surname: Martin fullname: Martin, Rainer E. organization: Medicinal Chemistry, Small Molecule Research, Pharma Research & Early Development (pRED), F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland) – sequence: 5 givenname: Robert surname: Britton fullname: Britton, Robert email: rbritton@sfu.ca organization: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia (Canada)
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/24668727$$D View this record in MEDLINE/PubMed
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Copyright	2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Keywords	EXCITED-STATE ACIDS amino acids REACTIVITY ALDEHYDES MEDICINAL CHEMISTRY ALKENES CH activation tungsten photochemistry polyoxometalates RADICALS PET ALKANES CH activation
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Notes	NSERC ArticleID:ANIE201400420 This work was supported by an NSERC Discovery Grant to R.B., a MSFHR Career Investigator Award to R.B., and NSERC Postgraduate Scholarships for S.D.H., H.F., S.C. MSFHR ark:/67375/WNG-D7V084KT-5 istex:F72B9EDF6F29E838408479F2F2F607EBDAB68448 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
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Snippet	Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site‐selective metabolic degradation of drugs and access... Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access...
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SubjectTerms	Amino acids Blocking Carbon - chemistry Catalysis Chemistry Chemistry, Multidisciplinary CH activation Derivatives Economics Fluorides Fluorination Fluorine - chemistry Fluorine Radioisotopes - chemistry Halogenation Hydrogen - chemistry Light Natural products Photocatalysis photochemistry Physical Sciences polyoxometalates Positron-Emission Tomography Science & Technology Sulfonamides - chemistry Tomography tungsten
Title	A Convenient Photocatalytic Fluorination of Unactivated CH Bonds
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