Literature DB >> 20000433

Dioxygen activation under ambient conditions: Cu-catalyzed oxidative amidation-diketonization of terminal alkynes leading to alpha-ketoamides.

Chun Zhang1, Ning Jiao.   

Abstract

A novel Cu-catalyzed oxidative amidation-diketonization reaction of terminal alkynes leading to alpha-ketoamides has been developed. This chemistry offers a valuable mechanistic insight into this novel Cu catalysis via a radical process. O(2) not only participates as the ideal oxidant but also undergoes dioxygen activation under ambient conditions in this transformation.

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Year:  2010        PMID： 20000433     DOI： 10.1021/ja908911n

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


  11 in total

1.  Oxidizable Ketones: Persistent Radical Cations from the Single-Electron Oxidation of 2,3-Diaminocyclopropenones.

Authors:  Zack M Strater; Michael Rauch; Steffen Jockusch; Tristan H Lambert
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-08       Impact factor: 15.336

Review 2.  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

Review 3.  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

4.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

5.  Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.

Authors:  Biao Lu; Chaoqun Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

6.  Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2017-10-16       Impact factor: 54.564

7.  A dinuclear palladium catalyst for α-hydroxylation of carbonyls with O2.

Authors:  Gary Jing Chuang; Weike Wang; Eunsung Lee; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2011-01-19       Impact factor: 15.419

8.  Uncovering the mechanism of the Ag(I)/persulfate-catalyzed cross-coupling reaction of arylboronic acids and heteroarenes.

Authors:  Niki R Patel; Robert A Flowers
Journal:  J Am Chem Soc       Date:  2013-03-18       Impact factor: 15.419

9.  Site-selective, catalytic, and diastereoselective sp3 C-H hydroxylation and alkoxylation of vicinally functionalized lactams.

Authors:  Timothy K Beng; Victoria Shearer; Rachel Davey; Ivianne Redman
Journal:  RSC Adv       Date:  2020-05-27       Impact factor: 4.036

10.  Computational exploration of copper catalyzed vinylogous aerobic oxidation of unsaturated compounds.

Authors:  Ting Wang; Yu Zhou; Yao Xu; Gui-Juan Cheng
Journal:  Sci Rep       Date:  2021-01-14       Impact factor: 4.379
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