Literature DB >> 27813242

Photoredox Activation of SF6 for Fluorination.

T Andrew McTeague1, Timothy F Jamison1.   

Abstract

We report the first practical use of SF6 as a fluorinating reagent in organic synthesis. Photoredox catalysis enables the in situ conversion of SF6 , an inert gas, into an active fluorinating species by using visible light. Under these conditions, deoxyfluorination of allylic alcohols is effected with high chemoselectivity and is tolerant of a wide range of functional groups. Application of the methodology in a continuous-flow setup achieves comparable yields to those obtained with a batch setup, while providing drastically increased material throughput of valuable allylic fluoride products.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; continuous flow; fluorination; photoredox catalysis; sulfur hexafluoride

Year:  2016        PMID: 27813242     DOI: 10.1002/anie.201608792

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


  15 in total

1.  The assembly and use of continuous flow systems for chemical synthesis.

Authors:  Joshua Britton; Timothy F Jamison
Journal:  Nat Protoc       Date:  2017-10-26       Impact factor: 13.491

2.  Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

Authors:  Mohammad B Khaled; Roukaya K El Mokadem; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

3.  Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations.

Authors:  Ren Wei Toh; Jie Sheng Li; Jie Wu
Journal:  J Vis Exp       Date:  2018-01-04       Impact factor: 1.355

Review 4.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

Review 5.  Repurposing of F-gases: challenges and opportunities in fluorine chemistry.

Authors:  Daniel J Sheldon; Mark R Crimmin
Journal:  Chem Soc Rev       Date:  2022-06-20       Impact factor: 60.615

Review 6.  Sulfur - fluorine bond in PET radiochemistry.

Authors:  Giancarlo Pascali; Lidia Matesic; Bo Zhang; Andrew T King; Andrea J Robinson; Alison T Ung; Benjamin H Fraser
Journal:  EJNMMI Radiopharm Chem       Date:  2017-07-17

7.  N-Acetylation of Amines in Continuous-Flow with Acetonitrile-No Need for Hazardous and Toxic Carboxylic Acid Derivatives.

Authors:  György Orsy; Ferenc Fülöp; István M Mándity
Journal:  Molecules       Date:  2020-04-23       Impact factor: 4.411

8.  Reaction discovery using acetylene gas as the chemical feedstock accelerated by the "stop-flow" micro-tubing reactor system.

Authors:  Fei Xue; Hongping Deng; Chengwen Xue; Dara Khairunnisa Binte Mohamed; Karen Yuanting Tang; Jie Wu
Journal:  Chem Sci       Date:  2017-02-27       Impact factor: 9.825

9.  Photoredox Catalytic α-Alkoxypentafluorosulfanylation of α-Methyl- and α-Phenylstyrene Using SF6.

Authors:  David Rombach; Hans-Achim Wagenknecht
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336

10.  Complete deconstruction of SF6 by an aluminium(I) compound.

Authors:  Daniel J Sheldon; Mark R Crimmin
Journal:  Chem Commun (Camb)       Date:  2021-07-20       Impact factor: 6.222

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