Literature DB >> 24038663

Functionalization of benzylic C(sp(3))-H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis.

Xingkuan Chen1, Song Yang, Bao-An Song, Yonggui Robin Chi.   

Abstract

Aryl aldehyde activation: Oxidative activation of 2-methylindole-3-carboxaldehyde (I) through N-heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho-quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C-H functionalization; N-heterocyclic carbenes; indoles; spiro compounds; synthetic methods

Mesh：

Substances：

Year:  2013        PMID： 24038663     DOI： 10.1002/anie.201305861

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


  10 in total

1.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

2.  Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.

Authors:  Ansoo Lee; Joshua L Zhu; Taisiia Feoktistova; Alexander C Brueckner; Paul H-Y Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

3.  N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors:  Dian-Feng Chen; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2016-11-18       Impact factor: 3.157

4.  Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles.

Authors:  Shao-Cong Zhan; Ren-Jie Fang; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2022-07-07       Impact factor: 2.544

5.  Thermal Hetero-Diels-Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones.

Authors:  Thomas Wurm; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  J Org Chem       Date:  2017-11-22       Impact factor: 4.354

6.  Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Pengcheng Zheng; Rakesh Ganguly; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2015-02-05       Impact factor: 14.919

7.  Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Yonggui Robin Chi
Journal:  Chem Sci       Date:  2015-07-20       Impact factor: 9.825

8.  N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides.

Authors:  Andreas Mavroskoufis; Keerthana Rajes; Paul Golz; Arush Agrawal; Vincent Ruß; Jan P Götze; Matthew N Hopkinson
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-09       Impact factor: 15.336

9.  Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones.

Authors:  Laura Carceller-Ferrer; Aleix González Del Campo; Carlos Vila; Gonzalo Blay; M Carmen Muñoz; José R Pedro
Journal:  J Org Chem       Date:  2022-03-16       Impact factor: 4.354

10.  Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

Authors:  Anna Lee; Ashkaan Younai; Christopher K Price; Javier Izquierdo; Rama K Mishra; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2014-07-15       Impact factor: 15.419
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.