Literature DB >> 24281908

Visible-light sensitization of vinyl azides by transition-metal photocatalysis.

Elliot P Farney1, Tehshik P Yoon.   

Abstract

Irradiation of vinyl and aryl azides with visible light in the presence of Ru photocatalysts results in the formation of reactive nitrenes, which can undergo a variety of C-N bond-forming reactions. The ability to use low-energy visible light instead of UV in the photochemical activation of azides avoids competitive photodecomposition processes that have long been a significant limitation on the synthetic use of these reactions.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  azides; energy transfer; nitrenes; nitrogen heterocycles; photocatalysis

Mesh：

Substances：

Year:  2013        PMID： 24281908      PMCID： PMC3905105          DOI： 10.1002/anie.201308820

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


  19 in total

1.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates.

Authors:  Alexander G O'Brien; François Lévesque; Peter H Seeberger
Journal:  Chem Commun (Camb)       Date:  2010-12-20       Impact factor: 6.222

3.  Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer.

Authors:  Mark S Tichenor; John D Trzupek; David B Kastrinsky; Futoshi Shiga; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

4.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

Review 5.  The interplay of theory and experiment in the study of phenylnitrene.

Authors:  W T Borden; N P Gritsan; C M Hadad; W L Karney; C R Kemnitz; M S Platz
Journal:  Acc Chem Res       Date:  2000-11       Impact factor: 22.384

6.  Visible light photocatalysis of [2+2] styrene cycloadditions by energy transfer.

Authors:  Zhan Lu; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-10       Impact factor: 15.336

7.  Structure and reactivity of benzoylnitrene radical anion in the gas phase.

Authors:  Neloni R Wijeratne; Paul G Wenthold
Journal:  J Org Chem       Date:  2007-11-15       Impact factor: 4.354

8.  Selective formation of triplet alkyl nitrenes from photolysis of beta-azido-propiophenone and their reactivity.

Authors:  Pradeep N D Singh; Sarah M Mandel; Jagadis Sankaranarayanan; Sivaramakrishnan Muthukrishnan; Mingxin Chang; Rachel M Robinson; Paul M Lahti; Bruce S Ault; Anna D Gudmundsdóttir
Journal:  J Am Chem Soc       Date:  2007-11-23       Impact factor: 15.419

9.  Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction.

Authors:  Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419

10.  A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system.

Authors:  Yiyun Chen; Adam S Kamlet; Jonathan B Steinman; David R Liu
Journal:  Nat Chem       Date:  2011-01-09       Impact factor: 24.427
View more
  20 in total

1.  Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer.

Authors:  Kazimer L Skubi; Jesse B Kidd; Hoimin Jung; Ilia A Guzei; Mu-Hyun Baik; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2017-11-16       Impact factor: 15.419

Review 2.  Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis.

Authors:  Bao Hu; Stephen G DiMagno
Journal:  Org Biomol Chem       Date:  2015-04-07       Impact factor: 3.876

3.  Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products.

Authors:  Xiao Zhang; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-12-14       Impact factor: 15.419

4.  Photocatalytic C-F Reduction and Functionalization.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

Review 5.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

6.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

7.  Spin-Selective Generation of Triplet Nitrenes: Olefin Aziridination through Visible-Light Photosensitization of Azidoformates.

Authors:  Spencer O Scholz; Elliot P Farney; Sangyun Kim; Desiree M Bates; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-06       Impact factor: 15.336

8.  Bromine Radical Catalysis by Energy Transfer Photosensitization.

Authors:  Dian-Feng Chen; Cameron H Chrisman; Garret M Miyake
Journal:  ACS Catal       Date:  2020-01-30       Impact factor: 13.084

9.  Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.

Authors:  Gabriele Fumagalli; Pauline T G Rabet; Scott Boyd; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-26       Impact factor: 15.336

10.  Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3-H functionalization.

Authors:  Wei Shu; Adriana Lorente; Enrique Gómez-Bengoa; Cristina Nevado
Journal:  Nat Commun       Date:  2017-01-13       Impact factor: 14.919
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.