Literature DB >> 29183109

Palladium-Catalyzed Dearomative syn-1,4-Carboamination.

Mikiko Okumura1, Alexander S Shved1, David Sarlah1.   

Abstract

A dearomative 1,4-carboamination of arenes has been achieved using arenophile cycloaddition and subsequent palladium-catalyzed substitution with nonstabilized lithium enolates. This protocol delivers products with exclusive syn-1,4-selectivity and can be also conducted in an asymmetric fashion. The method allows rapid dearomative difunctionalization of simple aromatic compounds into functional small molecules amenable to further diversification.

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Year:  2017        PMID： 29183109      PMCID： PMC5971112          DOI： 10.1021/jacs.7b11663

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


  39 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Ruthenium(II)-catalyzed C-H bond activation and functionalization.

Authors:  Percia Beatrice Arockiam; Christian Bruneau; Pierre H Dixneuf
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

3.  Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation.

Authors:  Bai-Lin Lei; Chang-Hua Ding; Xiao-Fei Yang; Xiao-Long Wan; Xue-Long Hou
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

4.  Sequential Tandem Addition to a Tungsten-Trifluorotoluene Complex: A Versatile Method for the Preparation of Highly Functionalized Trifluoromethylated Cyclohexenes.

Authors:  Katy B Wilson; Jeffery T Myers; Hannah S Nedzbala; Logan A Combee; Michal Sabat; W Dean Harman
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

5.  Rhodium-catalyzed ring-opening reactions of N-boc-azabenzonorbornadienes with amine nucleophiles.

Authors:  Yong-hwan Cho; Valentin Zunic; Hisanori Senboku; Madeline Olsen; Mark Lautens
Journal:  J Am Chem Soc       Date:  2006-05-31       Impact factor: 15.419

6.  Asymmetric catalysis with chiral ferrocene ligands.

Authors:  Li-Xin Dai; Tao Tu; Shu-Li You; Wei-Ping Deng; Xue-Long Hou
Journal:  Acc Chem Res       Date:  2003-09       Impact factor: 22.384

7.  New catalytic reactions of oxa- and azabicyclic alkenes.

Authors:  Dinesh Kumar Rayabarapu; Chien-Hong Cheng
Journal:  Acc Chem Res       Date:  2007-06-26       Impact factor: 22.384

8.  Rhodium-catalyzed asymmetric ring-opening alkynylation of azabenzonorbornadienes.

Authors:  Takahiro Nishimura; Eiji Tsurumaki; Takahiro Kawamoto; Xun-Xiang Guo; Tamio Hayashi
Journal:  Org Lett       Date:  2008-08-19       Impact factor: 6.005

9.  Optically active dinuclear palladium complexes containing a Pd-Pd bond: preparation and enantioinduction ability in asymmetric ring-opening reactions.

Authors:  Tomokazu Ogura; Kazuhiro Yoshida; Akira Yanagisawa; Tsuneo Imamoto
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  Iron-catalyzed dioxygen-driven C-C bond formation: oxidative dearomatization of 2-naphthols with construction of a chiral quaternary stereocenter.

Authors:  Takuya Oguma; Tsutomu Katsuki
Journal:  J Am Chem Soc       Date:  2012-11-30       Impact factor: 15.419
View more
  13 in total

1.  Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Authors:  Christopher J Huck; David Sarlah
Journal:  Chem       Date:  2020-07-01       Impact factor: 22.804

2.  Palladium-Catalyzed Dearomative syn-1,4-Diamination.

Authors:  William C Wertjes; Mikiko Okumura; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-21       Impact factor: 15.419

3.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

4.  Palladium-Catalyzed Dearomative syn-1,4-Oxyamination.

Authors:  Conghui Tang; Mikiko Okumura; Hejun Deng; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-20       Impact factor: 15.336

5.  Visible-Light-Induced Dearomatizations.

Authors:  Mikiko Okumura; David Sarlah
Journal:  European J Org Chem       Date:  2019-09-25

6.  Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

Authors:  Conghui Tang; Mikiko Okumura; Yunbo Zhu; Annie R Hooper; Yu Zhou; Yu-Hsuan Lee; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

7.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

8.  Arene dearomatization through a catalytic N-centered radical cascade reaction.

Authors:  Rory C McAtee; Efrey A Noten; Corey R J Stephenson
Journal:  Nat Commun       Date:  2020-05-20       Impact factor: 14.919

9.  Efficient Stereoselective Carbocyclization to cis-1,4-Disubstituted Heterocycles Enabled by Dual Pd/Electron Transfer Mediator (ETM) Catalysis.

Authors:  Can Zhu; Jie Liu; Binh Khanh Mai; Fahmi Himo; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2020-03-13       Impact factor: 15.419

Review 10.  Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles.

Authors:  Mario P Wiesenfeldt; Zackaria Nairoukh; Toryn Dalton; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-29       Impact factor: 15.336
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