Literature DB >> 35420241

Chiral Hemilabile P,N-Ligand-Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation.

Xiaohan Ye1, Chenhuan Wang1, Shuyao Zhang1, Qi Tang1, Lukasz Wojtas1, Minyong Li2, Xiaodong Shi1.   

Abstract

Enantioselective, intermolecular alkene arylamination was achieved through gold redox catalysis. Screening of ligands revealed chiral P,N ligands as the optimal choice, giving alkene aminoarylation with good yields (up to 80 %) and excellent stereoselectivity (up to 99 : 1 er). As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage, with the stereodetermining step (SDS) at the gold(III) intermediate, thus opening up a new way to conduct gold redox catalysis with stereochemistry control.
© 2022 Wiley-VCH GmbH.

Entities:  

Keywords:  alkenes; enantioselectivity; gold catalysis; hemilabile ligand; redox chemistry

Mesh:

Substances:

Year:  2022        PMID: 35420241      PMCID: PMC9254727          DOI: 10.1002/chem.202201018

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.020


  34 in total

1.  Gold-catalyzed homogeneous oxidative cross-coupling reactions.

Authors:  Guozhu Zhang; Yu Peng; Li Cui; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions.

Authors:  Manjur O Akram; Somsuvra Banerjee; Sagar S Saswade; Vaibhav Bedi; Nitin T Patil
Journal:  Chem Commun (Camb)       Date:  2018-10-02       Impact factor: 6.222

3.  Enantioselective aryl-aryl coupling facilitated by chiral binuclear gold complexes.

Authors:  Jonas Himmelstrup; Mikkel B Buendia; Xing-Wen Sun; Søren Kramer
Journal:  Chem Commun (Camb)       Date:  2019-10-24       Impact factor: 6.222

4.  Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors:  Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-07       Impact factor: 15.336

5.  Gold(I)/Gold(III) Catalysis Merging Oxidative Addition and π-Alkene Activation.

Authors:  Mathilde Rigoulet; Olivier Thillaye du Boullay; Abderrahmane Amgoune; Didier Bourissou
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-21       Impact factor: 15.336

6.  Intermolecular Alkene Difunctionalization via Gold-Catalyzed Oxyarylation.

Authors:  Shuyao Zhang; Chenhuan Wang; Xiaohan Ye; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-03       Impact factor: 15.336

7.  Gold-Catalyzed 1,2-Diarylation of Alkenes.

Authors:  Chetan C Chintawar; Amit K Yadav; Nitin T Patil
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-11       Impact factor: 15.336

8.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

9.  Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides.

Authors:  Abdallah Zeineddine; Laura Estévez; Sonia Mallet-Ladeira; Karinne Miqueu; Abderrahmane Amgoune; Didier Bourissou
Journal:  Nat Commun       Date:  2017-09-18       Impact factor: 14.919

10.  Synthesis of a Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis.

Authors:  Andrew W Heard; Stephen M Goldup
Journal:  Chem       Date:  2020-04-09       Impact factor: 22.804

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  1 in total

1.  Hemilabile MIC^N ligands allow oxidant-free Au(i)/Au(iii) arylation-lactonization of γ-alkenoic acids.

Authors:  Pau Font; Hugo Valdés; Gregorio Guisado-Barrios; Xavi Ribas
Journal:  Chem Sci       Date:  2022-07-22       Impact factor: 9.969

  1 in total

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