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  Transition-Metal-Mediated and Transition-Metal-Catalyzed Carbon–Fluorine Bond Formation

Neumann, C. N., & Ritter, T. (2020). Transition-Metal-Mediated and Transition-Metal-Catalyzed Carbon–Fluorine Bond Formation. In P. A. Evans (Ed.), Organic Reactions (pp. 613). John Wiley and Sons. doi:10.1002/0471264180.or104.03.

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 Creators:
Neumann, Constanze N.1, Author           
Ritter, Tobias2, Author           
Affiliations:
1Research Group Neumann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_3316369              
2Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040308              

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Free keywords: Transition-metal catalysis; fluorination; C–F bond formation; aryl fluoride; alkyl fluoride; nucleophilic fluorination; electrophilic fluorination
 Abstract: The number and diversity of methods for installing carbon–fluorine bonds have substantially expanded over the past two decades, enabling enantioselective fluorinations, reactions with complex substrates, and the use of ever simpler reaction precursors. Fluorination chemistry was long held back by unreactive alkali fluoride salts and highly reactive electrophilic fluorine sources, such as molecular fluorine and cobalt(III) fluoride. The introduction of fluorination reagents with controlled reactivity has been a key driving force in harnessing the reactivity of fluoride, as has the strategic use of transition metals. These approaches enable predictable and functional-group-tolerant carbon–fluorine bond formation. Herein, transition-metal-catalyzed and transition-metal-mediated syntheses of aromatic, heteroaromatic, and alkyl fluorides are reviewed. In addition, methods for allylic fluorination, benzylic fluorination, and fluorination α to carbonyl groups are presented. The influence of these reactions on the synthesis of complex fluorinated molecules and the preparation of 18F-PET probes are described, and experimental procedures for illustrative examples are included.

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Language(s): eng - English
 Dates: 2020-12-062020
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/0471264180.or104.03
 Degree: -

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Title: Organic Reactions
Source Genre: Series
 Creator(s):
Evans, P. Andrew1, Editor
Affiliations:
1 Chernoff Hall, Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario K7L 3N6, Canada, ou_persistent22            
Publ. Info: John Wiley and Sons
Pages: - Volume / Issue: 104 Sequence Number: - Start / End Page: 613 Identifier: ISBN: 978-1-119-65150-5