Literature DB >> 21381734

Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts.

John D Nguyen1, Joseph W Tucker, Marlena D Konieczynska, Corey R J Stephenson.   

Abstract

Atom transfer radical addition of haloalkanes and α-halocarbonyls to olefins is efficiently performed with the photocatalyst Ir[(dF(CF(3))ppy)(2)(dtbbpy)]PF(6). This protocol is characterized by excellent yields, mild conditions, low catalyst loading, and broad scope. In addition, the atom transfer protocol can be used to quickly and efficiently introduce vinyl trifluoromethyl groups to olefins and access 1,1-cyclopropane diesters.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21381734      PMCID： PMC3086499          DOI： 10.1021/ja108560e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  31 in total

1.  Visible light photoredox catalysis: applications in organic synthesis.

Authors:  Jagan M R Narayanam; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2010-06-08       Impact factor: 54.564

2.  Photoredox catalysis with visible light.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

4.  Electrostatic versus steric effects in peptidomimicry: synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres.

Authors:  Jingbo Xiao; Bernard Weisblum; Peter Wipf
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

5.  Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Authors:  Hui-Wen Shih; Mark N Vander Wal; Rebecca L Grange; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

6.  Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates.

Authors:  Laura Furst; Bryan S Matsuura; Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

7.  Triethylborane-induced bromine atom-transfer radical addition in aqueous media: study of the solvent effect on radical addition reactions.

Authors:  H Yorimitsu; H Shinokubo; S Matsubara; K Oshima; K Omoto; H Fujimoto
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

8.  Ruthenium catalysed cross metathesis with fluorinated olefins.

Authors:  S Imhof; S Randl; S Blechert
Journal:  Chem Commun (Camb)       Date:  2001-09-07       Impact factor: 6.222

9.  Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis.

Authors:  Juana Du; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

10.  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
View more
  53 in total

1.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

2.  Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

Authors:  Daria Kurandina; Mónica Rivas; Maxim Radzhabov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2018-01-05       Impact factor: 6.005

3.  Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes1.

Authors:  Deborah O Ayeni; Samir K Mandal; Barbara Zajc
Journal:  Tetrahedron Lett       Date:  2013-11-06       Impact factor: 2.415

4.  Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

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.  Lithium bis-catechol borate as an effective reductive quencher in photoredox catalysis.

Authors:  Martin J Sevrin; Laura Furst; John D Nguyen; James L Collins; Corey R J Stephenson
Journal:  Tetrahedron       Date:  2018-04-18       Impact factor: 2.457

7.  Visible-light photoredox catalysis in flow.

Authors:  Joseph W Tucker; Yuan Zhang; Timothy F Jamison; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-16       Impact factor: 15.336

8.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

9.  The Development of Visible-Light Photoredox Catalysis in Flow.

Authors:  Zachary J Garlets; John D Nguyen; Corey R J Stephenson
Journal:  Isr J Chem       Date:  2014-04-01       Impact factor: 3.333

10.  Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Authors:  Giulia Bergonzini; Corinna S Schindler; Carl-Johan Wallentin; Eric N Jacobsen; Corey R J Stephenson
Journal:  Chem Sci       Date:  2014-01       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.