ChemInform Abstract: A Convenient Photocatalytic Fluorination of Unactivated C—H Bonds.

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

doi:10.1002/chin.201445048

Cited by 2 publications

(1 citation statement)

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“…A different approach to acyl fluorides was followed by Britton et al using the decatungstate photocatalyst and the electrophilic fluorinating agent N-fluorobenzenesulfonimide (NFSI) [271]. Through decatungstate photocatalysis, site-Scheme 80 Electrochemical continuous flow synthesis of 1,4benzoxathiins and 1,4benzothiazines selective C − H fluorination was achieved for both unactivated and activated C − H bonds, the methodology also being applied to the synthesis of tracers for Positron Emission Tomography (PET) studies by the labelling of amino acids and peptides with [ 18 F]NFSI [272][273][274]. Notable is the difference in selectivity obtained when using photocatalysis when compared to a thermal radical chain reaction initiated with AIBN, exemplified by the functionalization of 4ethyltoluene bearing two distinct benzylic positions, with AIBN favouring methyl functionalization (kinetic control).…”

Section: − H Fluorinationmentioning

confidence: 99%

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

2020

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C-H functionalization chemistry is one of the most vibrant research areas within synthetic organic chemistry. While most researchers focus on the development of small-scale batch-type transformations, more recently such transformations have been carried out in flow reactors to explore new chemical space, to boost reactivity or to enable scalability of this important reaction class. Herein, an up-to-date overview of C-H bond functionalization reactions carried out in continuous-flow microreactors is presented. A comprehensive overview of reactions which establish the formal conversion of a C-H bond into carbon-carbon or carbonheteroatom bonds is provided; this includes metal-assisted C-H bond cleavages, hydrogen atom transfer reactions and C-H bond functionalizations which involve an S E-type process to aromatic or olefinic systems. Particular focus is devoted to showcase the advantages of flow processing to enhance C-H bond functionalization chemistry. Consequently, it is our hope that this review will serve as a guide to inspire researchers to push the boundaries of C-H functionalization chemistry using flow technology.

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Section: − H Fluorinationmentioning

confidence: 99%