Literature DB >> 29544244

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

Lucas W Hernandez1, Ulrich Klöckner1, Jola Pospech1, Lilian Hauss1, David Sarlah1.   

Abstract

We describe the development of an arenophile-mediated, nickel-catalyzed dearomative trans-1,2-carboamination protocol. A range of readily available aromatic compounds was converted to the corresponding dienes using Grignard reagents as nucleophiles. This strategy provided products with exclusive trans-selectivity and high enantioselectivity was observed in case of benzene and naphthalene. The utility of this methodology was showcased by controlled and stereoselective preparation of small, functionalized molecules.

Entities:  

Mesh：

Substances：

Year:  2018        PMID： 29544244      PMCID： PMC5971658          DOI： 10.1021/jacs.8b01726

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


  55 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.  On the origin of the haouamine alkaloids.

Authors:  Noah Z Burns; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Hydroamination: direct addition of amines to alkenes and alkynes.

Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal:  Chem Rev       Date:  2008-08-26       Impact factor: 60.622

Review 4.  The economies of synthesis.

Authors:  Timothy Newhouse; Phil S Baran; Reinhard W Hoffmann
Journal:  Chem Soc Rev       Date:  2009-08-21       Impact factor: 54.564

5.  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

Review 6.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       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.  Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.

Authors:  Chris E Houlden; Chris D Bailey; J Gair Ford; Michel R Gagné; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2008-07-10       Impact factor: 15.419

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
  10 in total

1.  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

2.  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

3.  Visible-Light-Induced Dearomatizations.

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

4.  Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors:  Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

5.  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

6.  Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes.

Authors:  Ping Yang; Chao Zheng; Yu-Han Nie; Shu-Li You
Journal:  Chem Sci       Date:  2020-06-10       Impact factor: 9.825

7.  Computational assessments of diastereoselective [4+2] cycloaddition and 1,3-borotopic shift of a dearomatized tertiary boronic ester intermediate: reactivities explained through transition-state distortion energies.

Authors:  Aqeel A Hussein; Faisal A Almalki; Alaa M Alqahtani; Sergey Shityakov
Journal:  RSC Adv       Date:  2019-07-26       Impact factor: 4.036

8.  Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization.

Authors:  Peng Ji; Cassondra C Davies; Feng Gao; Jing Chen; Xiang Meng; Kendall N Houk; Shuming Chen; Wei Wang
Journal:  Nat Commun       Date:  2022-08-05       Impact factor: 17.694

Review 9.  Recent Visible Light and Metal Free Strategies in [2+2] and [4+2] Photocycloadditions.

Authors:  Marina Sicignano; Ricardo I Rodríguez; José Alemán
Journal:  European J Org Chem       Date:  2021-06-10

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
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.