Literature DB >> 25143256

Visible light-promoted metal-free sp(3)-C-H fluorination.

Ji-Bao Xia1, Chen Zhu, Chuo Chen.   

Abstract

Photoexcited acetophenone can catalyze the fluorination of unactivated C(sp(3))-H groups. While acetophenone, a colorless oil, only has a trace amount of absorption in the visible light region, its photoexcitation can be achieved by irradiation with light generated by a household compact fluorescent lamp (CFL). This operational simple method provides improved substrate scope for the direct incorporation of a fluorine atom into simple organic molecules. CFL-irradiation can also be used to promote certain classic UV-promoted photoreactions of colorless monoarylketones and enones/enals.

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Year:  2014        PMID: 25143256      PMCID: PMC4160356          DOI: 10.1039/c4cc05650g

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


  35 in total

1.  The effects of UV emission from compact fluorescent light exposure on human dermal fibroblasts and keratinocytes in vitro.

Authors:  Tatsiana Mironava; Michael Hadjiargyrou; Marcia Simon; Miriam H Rafailovich
Journal:  Photochem Photobiol       Date:  2012-07-20       Impact factor: 3.421

2.  Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors:  Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

3.  Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes.

Authors:  Elena Arceo; Igor D Jurberg; Ana Alvarez-Fernández; Paolo Melchiorre
Journal:  Nat Chem       Date:  2013-08-11       Impact factor: 24.427

4.  Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

Authors:  Kelvin S L Chan; Masayuki Wasa; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

Review 5.  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

6.  Direct, catalytic monofluorination of sp³ C-H bonds: a radical-based mechanism with ionic selectivity.

Authors:  Cody Ross Pitts; Steven Bloom; Ryan Woltornist; Dillon Jay Auvenshine; Lev R Ryzhkov; Maxime A Siegler; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2014-06-27       Impact factor: 15.419

Review 7.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

8.  A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

Authors:  Ji-Bao Xia; Kevin W Cormier; Chuo Chen
Journal:  Chem Sci       Date:  2012-04-13       Impact factor: 9.825

9.  Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

Authors:  Jennifer L Roizen; Mark Edwin Harvey; J Du Bois
Journal:  Acc Chem Res       Date:  2012-04-30       Impact factor: 22.384

10.  Vanadium-Catalyzed C(sp3)-H Fluorination Reactions.

Authors:  Ji-Bao Xia; Yuyong Ma; Chuo Chen
Journal:  Org Chem Front       Date:  2014-07-01       Impact factor: 5.281

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  17 in total

1.  Ketone-catalyzed photochemical C(sp3)-H chlorination.

Authors:  Lei Han; Jibao Xia; Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-05-04       Impact factor: 2.457

2.  Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.

Authors:  Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-12-15       Impact factor: 2.457

3.  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

4.  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

5.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

6.  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

7.  The past, present, and future of the Yang reaction.

Authors:  Chuo Chen
Journal:  Org Biomol Chem       Date:  2016-08-12       Impact factor: 3.876

8.  Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

Authors:  Cody Ross Pitts; Michelle Sheanne Bloom; Desta Doro Bume; Qinze Arthur Zhang; Thomas Lectka
Journal:  Chem Sci       Date:  2015-06-23       Impact factor: 9.825

9.  Photoredox ketone catalysis for the direct C-H imidation and acyloxylation of arenes.

Authors:  Chandra Bhushan Tripathi; Tsuyoshi Ohtani; Michael T Corbett; Takashi Ooi
Journal:  Chem Sci       Date:  2017-06-05       Impact factor: 9.825

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

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

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