Literature DB >> 30653314

Mechanism of Photoredox-Initiated C-C and C-N Bond Formation by Arylation of IPrAu(I)-CF3 and IPrAu(I)-Succinimide.

Suhong Kim1, F Dean Toste1.   

Abstract

Herein, we report on the photoredox-initiated gold-mediated <span class="Chemical">C(sp2)n>-CF3 and <span class="Chemical">C(sp2)-N coupling reactions. By adopting gold as a platform for probing <span class="Chemical">metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C-C and C-N coupling reactions. The high-valent gold(III) intermediates are accessed by virtue of photoredox catalysis through a radical chain process. In addition, the bond-forming step of the coupling reactions is the reductive elimination from cationic gold(III) intermediates, which is supported by isolation and crystallographic characterization of key Au(III) intermediates.

Entities:  

Year:  2019        PMID： 30653314      PMCID： PMC6446566          DOI： 10.1021/jacs.8b11273

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


  65 in total

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Authors:  Yingda Ye; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

Review 2.  A "Renaissance" in radical trifluoromethylation.

Authors:  Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-13       Impact factor: 15.336

3.  Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides.

Authors:  Jesse W Tye; Zhiqiang Weng; Adam M Johns; Christopher D Incarvito; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-07-03       Impact factor: 15.419

4.  Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis.

Authors:  Dipannita Kalyani; Kate B McMurtrey; Sharon R Neufeldt; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2011-11-02       Impact factor: 15.419

5.  Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis.

Authors:  David A Nagib; David W C MacMillan
Journal:  Nature       Date:  2011-12-08       Impact factor: 49.962

6.  New Methods of Free-Radical Perfluoroalkylation of Aromatics and Alkenes. Absolute Rate Constants and Partial Rate Factors for the Homolytic Aromatic Substitution by n-Perfluorobutyl Radical.

Authors:  Anna Bravo; Hans-René Bjørsvik; Francesca Fontana; Lucia Liguori; Andrea Mele; Francesco Minisci
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

7.  Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

Authors:  Amanda E King; Lauren M Huffman; Alicia Casitas; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

8.  Mechanistic studies on the copper-catalyzed N-arylation of amides.

Authors:  Eric R Strieter; Brijesh Bhayana; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

9.  Carbon-nitrogen bond formation involving well-defined aryl-copper(III) complexes.

Authors:  Lauren M Huffman; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

10.  Recent progress in the generation and use of nitrogen-centred radicals.

Authors:  Samir Z Zard
Journal:  Chem Soc Rev       Date:  2008-06-17       Impact factor: 54.564
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  4 in total

1.  Homogeneous Gold Redox Chemistry: Organometallics, Catalysis, and Beyond.

Authors:  Banruo Huang; Mingyou Hu; F Dean Toste
Journal:  Trends Chem       Date:  2020-06-02

Review 2.  Light-Induced Mechanistic Divergence in Gold(I) Catalysis: Revisiting the Reactivity of Diazonium Salts.

Authors:  Svenja Taschinski; René Döpp; Martin Ackermann; Frank Rominger; Folkert de Vries; Maximilian F S J Menger; Matthias Rudolph; A Stephen K Hashmi; Johannes E M N Klein
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-11       Impact factor: 15.336

3.  Trifluoromethylation of [AuF3 (SIMes)]: Preparation and Characterization of [Au(CF3 )x F3-x (SIMes)] (x=1-3) Complexes.

Authors:  Marlon Winter; Niklas Limberg; Mathias A Ellwanger; Alberto Pérez-Bitrián; Karsten Sonnenberg; Simon Steinhauer; Sebastian Riedel
Journal:  Chemistry       Date:  2020-10-27       Impact factor: 5.236

4.  Mechanistic Investigation and Optimization of Photoredox Anti-Markovnikov Hydroamination.

Authors:  Yangzhong Qin; Qilei Zhu; Rui Sun; Jacob M Ganley; Robert R Knowles; Daniel G Nocera
Journal:  J Am Chem Soc       Date:  2021-06-30       Impact factor: 16.383
  4 in total

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