Literature DB >> 33599472

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors.

Jiarong Shi1, Lianggui Li1, Yang Li1.   

Abstract

Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

Entities:  

Year:  2021        PMID: 33599472     DOI: 10.1021/acs.chemrev.0c01011

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  13 in total

Review 1.  Diels-Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry.

Authors:  Stanisław Krompiec; Aneta Kurpanik-Wójcik; Marek Matussek; Bogumiła Gołek; Angelika Mieszczanin; Aleksandra Fijołek
Journal:  Materials (Basel)       Date:  2021-12-27       Impact factor: 3.623

2.  "Kobayashi Benzynes" as Hexadehydro-Diels-Alder Diynophiles.

Authors:  Sahil Arora; Thomas R Hoye
Journal:  Org Lett       Date:  2021-04-22       Impact factor: 6.005

3.  Arylhydrazine Trapping of Benzynes: Mechanistic Insights and a Route to Azoarenes.

Authors:  Dorian S Sneddon; Thomas R Hoye
Journal:  Org Lett       Date:  2021-04-19       Impact factor: 6.005

4.  Interception of 1,2-cyclohexadiene with TEMPO radical.

Authors:  Matthew S McVeigh; Neil K Garg
Journal:  Tetrahedron Lett       Date:  2021-11-15       Impact factor: 2.415

5.  Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.

Authors:  Melissa Ramirez; Evan R Darzi; Joyann S Donaldson; Kendall N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-06       Impact factor: 16.823

Review 6.  Metal-Catalyzed Haloalkynylation Reactions.

Authors:  Mathis Kreuzahler; Gebhard Haberhauer
Journal:  Chemistry       Date:  2021-11-18       Impact factor: 5.020

7.  Palladium-Catalyzed Annulations of Strained Cyclic Allenes.

Authors:  Andrew V Kelleghan; Dominick C Witkowski; Matthew S McVeigh; Neil K Garg
Journal:  J Am Chem Soc       Date:  2021-06-18       Impact factor: 16.383

8.  Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives.

Authors:  Qile Wang; Thomas R Hoye
Journal:  Org Lett       Date:  2021-06-28       Impact factor: 6.072

9.  The Aryne Phosphate Reaction.

Authors:  Thomas M Haas; Stefan Wiesler; Tobias Dürr-Mayer; Alexander Ripp; Paraskevi Fouka; Danye Qiu; Henning J Jessen
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-22       Impact factor: 16.823

Review 10.  Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.

Authors:  Sarah M Anthony; Laura G Wonilowicz; Matthew S McVeigh; Neil K Garg
Journal:  JACS Au       Date:  2021-06-23
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