Literature DB >> 22789112

Copper-catalyzed aerobic aliphatic C-H oxygenation directed by an amidine moiety.

Yi-Feng Wang1, Hui Chen, Xu Zhu, Shunsuke Chiba.   

Abstract

A method for the oxygenation of tertiary C-H bonds of N-alkylamidines and N-(2-alkylaryl)amidines is described that utilizes the CuBr·SMe(2)/2,2'-bipyridine catalytic system under an O(2) atmosphere and provides dihydrooxazoles and 4H-1,3-benzoxazines. The oxygen atom is incorporated from atmospheric molecular oxygen during the present process.

Entities:  

Year:  2012        PMID： 22789112     DOI： 10.1021/ja305833a

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


  19 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Synlett       Date:  2019-11-27       Impact factor: 2.454

3.  General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

Authors:  Padon Chuentragool; Marvin Parasram; Yi Shi; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

Review 4.  Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

Review 5.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

6.  Catalytic Alkene Difunctionalization via Imidate Radicals.

Authors:  Kohki M Nakafuku; Stacy C Fosu; David A Nagib
Journal:  J Am Chem Soc       Date:  2018-08-29       Impact factor: 15.419

7.  Directed β C-H Amination of Alcohols via Radical Relay Chaperones.

Authors:  Ethan A Wappes; Kohki M Nakafuku; David A Nagib
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

8.  Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Authors:  Leah M Stateman; Kohki M Nakafuku; David A Nagib
Journal:  Synthesis (Stuttg)       Date:  2018-02-12       Impact factor: 3.157

9.  Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3 )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.

Authors:  Maxim Ratushnyy; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

10.  Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C-N/C-O-forming cascade.

Authors:  Quintin Elliott; Gabriel Dos Passos Gomes; Christopher J Evoniuk; Igor V Alabugin
Journal:  Chem Sci       Date:  2020-02-21       Impact factor: 9.825
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