Literature DB >> 32037616

Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.

Jin Wang1, Chiyu Wei2, Xuming Li2, Pengyi Zhao3, Chuan Shan2, Lukasz Wojtas2, Hao Chen3, Xiaodong Shi2.   

Abstract

Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkyne; allene; diselenation; gold redox catalysis; mild oxidant

Year:  2020        PMID： 32037616      PMCID： PMC7220824          DOI： 10.1002/chem.202000166

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  56 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.  Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines.

Authors:  Manjur O Akram; Avishek Das; Indradweep Chakrabarty; Nitin T Patil
Journal:  Org Lett       Date:  2019-09-26       Impact factor: 6.005

3.  Facile oxidative addition of aryl iodides to gold(I) by ligand design: bending turns on reactivity.

Authors:  Maximilian Joost; Abdallah Zeineddine; Laura Estévez; Sonia Mallet-Ladeira; Karinne Miqueu; Abderrahmane Amgoune; Didier Bourissou
Journal:  J Am Chem Soc       Date:  2014-10-08       Impact factor: 15.419

4.  On the Accessible Reaction Channels of Vinyl Gold(I) Species: π- and σ-Pathways.

Authors:  Laura Nunes Dos Santos Comprido; Johannes E M N Klein; Gerald Knizia; Johannes Kästner; A Stephen K Hashmi
Journal:  Chemistry       Date:  2017-07-19       Impact factor: 5.236

5.  Oxidative Intramolecular 1,2-Amino-Oxygenation of Alkynes under AuI /AuIII Catalysis: Discovery of a Pyridinium-Oxazole Dyad as an Ionic Fluorophore.

Authors:  Aslam C Shaikh; Dnyanesh S Ranade; Pattuparambil R Rajamohanan; Prasad P Kulkarni; Nitin T Patil
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-21       Impact factor: 15.336

6.  Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach.

Authors:  Xiaohan Ye; Pengyi Zhao; Shuyao Zhang; Yanbin Zhang; Qilin Wang; Chuan Shan; Lukasz Wojtas; Hao Guo; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-04       Impact factor: 15.336

Review 7.  Organoselenium and organotellurium compounds: toxicology and pharmacology.

Authors:  Cristina W Nogueira; Gilson Zeni; João B T Rocha
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

8.  Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant.

Authors:  Rong Cai; Mei Lu; Ellen Y Aguilera; Yumeng Xi; Novruz G Akhmedov; Jeffrey L Petersen; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-05       Impact factor: 15.336

9.  Fully Relativistic, Comparative Investigation of Gold and Platinum Alkyne Complexes of Relevance for the Catalysis of Nucleophilic Additions to Alkynes.

Authors:  Markus Pernpointner; A Stephen K Hashmi
Journal:  J Chem Theory Comput       Date:  2009-09-21       Impact factor: 6.006

10.  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
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