Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Direct photocatalytic fluorination of benzylic C-H bonds with N-fluorobenzenesulfonimide.

Literature DB >> 26107990

Direct photocatalytic fluorination of benzylic C-H bonds with N-fluorobenzenesulfonimide.

Matthew B Nodwell¹, Abhimanyu Bagai, Shira D Halperin, Rainer E Martin, Henner Knust, Robert Britton.

Abstract

The late-stage fluorination of common synthetic building blocks and drug leads is an appealing reaction for medicinal chemistry. In particular, fluorination of benzylic C-H bonds provides a means to attenuate drug metabolism at this metabolically labile position. Here we report two complimentary strategies for the direct fluorination of benzylic C-H bonds using N-fluorobenzenesulfonimide and either a decatungstate photocatalyst or AIBN-initiation.

Entities: Chemical

Mesh：

Substances：

Year: 2015 PMID： 26107990 DOI： 10.1039/c5cc04058b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

Keyword Cloud
Cited

14 in total

1. 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

2. Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors: Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal: Nat Rev Chem Date: 2022-05-17 Impact factor: 34.571

3. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

Authors: Stefan Andrew Harry; Michael Richard Xiang; Eric Holt; Andrea Zhu; Fereshte Ghorbani; Dhaval Patel; Thomas Lectka
Journal: Chem Sci Date: 2022-05-30 Impact factor: 9.969

4. 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

5. Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

Authors: Joshua A Buss; Aristidis Vasilopoulos; Dung L Golden; Shannon S Stahl
Journal: Org Lett Date: 2020-07-29 Impact factor: 6.005

6. Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles.

Authors: Aristidis Vasilopoulos; Dung L Golden; Joshua A Buss; Shannon S Stahl
Journal: Org Lett Date: 2020-07-29 Impact factor: 6.005

Direct photocatalytic fluorination of benzylic C-H bonds with N-fluorobenzenesulfonimide.

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

2. Radical C(sp3)-H functionalization and cross-coupling reactions.

3. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

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

5. Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

6. Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles.

7. N-Directed fluorination of unactivated Csp³-H bonds.

Review 8. Photoredox-Catalyzed C-H Functionalization Reactions.

9. Cu-Catalyzed aromatic C-H imidation with N-fluorobenzenesulfonimide: mechanistic details and predictive models.

Review 10. Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.