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Literature DB >> 23355453

NHC-catalyzed hydroacylation of styrenes.

Michael Schedler¹, Duo-Sheng Wang, Frank Glorius.

Abstract

New hydroacylation catalysts: Highly electron-rich N-heterocyclic carbenes (NHCs) facilitate the intermolecular hydroacylation of unstrained olefins. This unprecedented organocatalytic coupling joins simple and abundant aldehydes and styrenes to yield valuable ketone products. EWG=electron-withdrawing group, EDG=electron-donating group.

Entities: Chemical Disease

Year: 2013 PMID： 23355453 DOI： 10.1002/anie.201209291

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

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Cited

11 in total

Review 1. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors: Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal: Chem Rev Date: 2015-05-20 Impact factor: 60.622

2. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors: Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal: Chem Sci Date: 2014-05-01 Impact factor: 9.825

3. Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

Authors: Yujing Zhou; Jeffrey S Bandar; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2017-06-06 Impact factor: 15.419

4. An overview of N-heterocyclic carbenes.

Authors: Matthew N Hopkinson; Christian Richter; Michael Schedler; Frank Glorius
Journal: Nature Date: 2014-06-26 Impact factor: 49.962

5. Substrate-directed hydroacylation: rhodium-catalyzed coupling of vinylphenols and nonchelating aldehydes.

Authors: Stephen K Murphy; Achim Bruch; Vy M Dong
Journal: Angew Chem Int Ed Engl Date: 2014-01-29 Impact factor: 15.336

6. Well-Defined and Robust Rhodium Catalysts for the Hydroacylation of Terminal and Internal Alkenes.

Authors: Amparo Prades; Maitane Fernández; Sebastian D Pike; Michael C Willis; Andrew S Weller
Journal: Angew Chem Int Ed Engl Date: 2015-06-09 Impact factor: 15.336

7. Mechanistic insights into hydroacylation with non-chelating aldehydes†Electronic supplementary information (ESI) available: Materials and methods, reaction procedures, characterization data. CCDC 1012849. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02026jClick here for additional data file.

Authors: Stephen K Murphy; Achim Bruch; Vy M Dong
Journal: Chem Sci Date: 2014-09-22 Impact factor: 9.825

8. Mechanistic Insight Into the AuCN Catalyzed Annulation Reaction of Salicylaldehyde and Aryl Acetylene: Cyanide Ion Promoted Umpolung Hydroacylation/Intramolecular Oxa-Michael Addition Mechanism.

Authors: Manyi Yang; Guoqiang Wang; Jingxiang Zou; Shuhua Li
Journal: Front Chem Date: 2019-08-06 Impact factor: 5.221

9. Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

Authors: Qing-An Chen; Daniel K Kim; Vy M Dong
Journal: J Am Chem Soc Date: 2014-03-03 Impact factor: 15.419

10. NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones.

Authors: Ken Takaki; Makoto Hino; Akira Ohno; Kimihiro Komeyama; Hiroto Yoshida; Hiroshi Fukuoka
Journal: Beilstein J Org Chem Date: 2017-08-30 Impact factor: 2.883