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Literature DB >> 27320442

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

Julian G West¹, T Aaron Bedell¹, Erik J Sorensen².

Abstract

The fluorination of unactivated C(sp(3) )-H bonds remains a desirable and challenging transformation for pharmaceutical, agricultural, and materials scientists. Previous methods for this transformation have used bench-stable fluorine atom sources; however, many still rely on the use of UV-active photocatalysts for the requisite high-energy hydrogen atom abstraction event. Uranyl nitrate hexahydrate is described as a convenient, hydrogen atom abstraction catalyst that can mediate fluorinations of certain alkanes upon activation with visible light.

Entities: Chemical Disease Species

Keywords: C−H activation; fluorination; hydrogen atom transfer; photocatalysis; uranium

Year: 2016 PMID： 27320442 PMCID： PMC5091084 DOI： 10.1002/anie.201603149

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

18 in total

Review 1. Towards uranium catalysts.

Authors: Alexander R Fox; Suzanne C Bart; Karsten Meyer; Christopher C Cummins
Journal: Nature Date: 2008-09-18 Impact factor: 49.962

2. Organic fluorine compounds: a great opportunity for enhanced materials properties.

Authors: Ricarda Berger; Giuseppe Resnati; Pierangelo Metrangolo; Edwin Weber; Jürg Hulliger
Journal: Chem Soc Rev Date: 2011-03-30 Impact factor: 54.564

3. A polycomponent metal-catalyzed aliphatic, allylic, and benzylic fluorination.

Authors: Steven Bloom; Cody Ross Pitts; David Curtin Miller; Nathan Haselton; Maxwell Gargiulo Holl; Ellen Urheim; Thomas Lectka
Journal: Angew Chem Int Ed Engl Date: 2012-09-13 Impact factor: 15.336

Review 4. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

5. The C-H and alpha(C-X) bond dissociation enthalpies of toluene, C6H5-CH2X (X = F, Cl), and their substituted derivatives: a DFT study.

Authors: Pham-Cam Nam; Minh Tho Nguyen; Asit K Chandra
Journal: J Phys Chem A Date: 2005-11-17 Impact factor: 2.781

6. Roles of acetone and diacetone alcohol in coordination and dissociation reactions of uranyl complexes.

Authors: Daniel Rios; George Schoendorff; Michael J Van Stipdonk; Mark S Gordon; Theresa L Windus; John K Gibson; Wibe A de Jong
Journal: Inorg Chem Date: 2012-11-12 Impact factor: 5.165

7. Fluorine transfer to alkyl radicals.

Authors: Montserrat Rueda-Becerril; Claire Chatalova Sazepin; Joe C T Leung; Tulin Okbinoglu; Pierre Kennepohl; Jean-François Paquin; Glenn M Sammis
Journal: J Am Chem Soc Date: 2012-02-22 Impact factor: 15.419

8. Oxidative aliphatic C-H fluorination with fluoride ion catalyzed by a manganese porphyrin.

Authors: Wei Liu; Xiongyi Huang; Mu-Jeng Cheng; Robert J Nielsen; William A Goddard; John T Groves
Journal: Science Date: 2012-09-14 Impact factor: 47.728

9. Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.

Authors: Ji-Bao Xia; Chen Zhu; Chuo Chen
Journal: J Am Chem Soc Date: 2013-11-12 Impact factor: 15.419

10. Trifluoromethyl ethers--synthesis and properties of an unusual substituent.

Authors: Frédéric R Leroux; Baptiste Manteau; Jean-Pierre Vors; Sergiy Pazenok
Journal: Beilstein J Org Chem Date: 2008-04-29 Impact factor: 2.883

13 in total

1. 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

2. 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

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

Review 1. Towards uranium catalysts.

2. Organic fluorine compounds: a great opportunity for enhanced materials properties.

3. A polycomponent metal-catalyzed aliphatic, allylic, and benzylic fluorination.

Review 4. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

5. The C-H and alpha(C-X) bond dissociation enthalpies of toluene, C6H5-CH2X (X = F, Cl), and their substituted derivatives: a DFT study.

6. Roles of acetone and diacetone alcohol in coordination and dissociation reactions of uranyl complexes.

7. Fluorine transfer to alkyl radicals.

8. Oxidative aliphatic C-H fluorination with fluoride ion catalyzed by a manganese porphyrin.

9. Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.

10. Trifluoromethyl ethers--synthesis and properties of an unusual substituent.

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

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

3. Uranyl dication mediated photoswitching of a calix[4]pyrrole-based metal coordination cage.

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

Review 5. Photoredox-Catalyzed C-H Functionalization Reactions.

Review 6. Challenges and opportunities for alkane functionalisation using molecular catalysts.

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

8. Ketones as directing groups in photocatalytic sp³ C-H fluorination.

Review 9. Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis.

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