Literature DB >> 24668727

A convenient photocatalytic fluorination of unactivated C-H bonds.

Shira D Halperin1, Hope Fan, Stanley Chang, Rainer E Martin, Robert Britton.   

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 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.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; amino acids; photochemistry; polyoxometalates; tungsten

Mesh:

Substances:

Year:  2014        PMID: 24668727     DOI: 10.1002/anie.201400420

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  36 in total

1.  Ketone-catalyzed photochemical C(sp3)-H chlorination.

Authors:  Lei Han; Jibao Xia; Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-05-04       Impact factor: 2.457

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Visible light-promoted metal-free sp(3)-C-H fluorination.

Authors:  Ji-Bao Xia; Chen Zhu; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-10-11       Impact factor: 6.222

4.  C-H fluorination: U can fluorinate unactivated bonds.

Authors:  Constanze N Neumann; Tobias Ritter
Journal:  Nat Chem       Date:  2016-08-24       Impact factor: 24.427

5.  The Uranyl Cation as a Visible-Light Photocatalyst for C(sp(3) )-H Fluorination.

Authors:  Julian G West; T Aaron Bedell; Erik J Sorensen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

6.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

7.  A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis.

Authors:  Kaila A Margrey; William L Czaplyski; David A Nicewicz; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2018-03-16       Impact factor: 15.419

8.  Site-Selective Aliphatic C-H Chlorination Using N-Chloroamides Enables a Synthesis of Chlorolissoclimide.

Authors:  Ryan K Quinn; Zef A Könst; Sharon E Michalak; Yvonne Schmidt; Anne R Szklarski; Alex R Flores; Sangkil Nam; David A Horne; Christopher D Vanderwal; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2016-01-06       Impact factor: 15.419

9.  18F-Branched-Chain Amino Acids: Structure-Activity Relationships and PET Imaging Potential.

Authors:  Matthew B Nodwell; Hua Yang; Helen Merkens; Noeen Malik; Milena Čolović; Rainer E Martin; François Bénard; Paul Schaffer; Robert Britton
Journal:  J Nucl Med       Date:  2019-01-25       Impact factor: 10.057

10.  Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

Authors:  Crystal K Chu; Daniel T Ziegler; Brian Carr; Zachary K Wickens; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-25       Impact factor: 15.336

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