Literature DB >> 23132413

Use of benzynes for the synthesis of heterocycles.

Anton V Dubrovskiy1, Nataliya A Markina, Richard C Larock.   

Abstract

About two decades after Kobayashi's discovery in 1983 of a very mild way of generating highly reactive aryne intermediates, the synthetic community embraced o-(trimethylsilyl)aryl triflates as convenient and versatile aryne precursors for the synthesis of carbocycles and heterocycles, as well as natural products and pharmaceutically promising drug candidates. This review provides a comprehensive overview of the construction of heterocycles using Kobayashi's silylaryl triflate aryne precursors. It is organized according to the type of heterocycle generated.

Entities:  

Year:  2012        PMID: 23132413     DOI: 10.1039/c2ob26673c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  34 in total

1.  Expanding the ROMP Toolbox: Synthesis of Air-Stable Benzonorbornadiene Polymers by Aryne Chemistry.

Authors:  Jose M Medina; Jeong Hoon Ko; Heather D Maynard; Neil K Garg
Journal:  Macromolecules       Date:  2017-01-04       Impact factor: 5.985

2.  Computational predictions of substituted benzyne and indolyne regioselectivities.

Authors:  Elias Picazo; K N Houk; Neil K Garg
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Diels-Alder cycloadditions of strained azacyclic allenes.

Authors:  Joyann S Barber; Michael M Yamano; Melissa Ramirez; Evan R Darzi; Rachel R Knapp; Fang Liu; K N Houk; Neil K Garg
Journal:  Nat Chem       Date:  2018-07-30       Impact factor: 24.427

4.  Quantification of the Electrophilicity of Benzyne and Related Intermediates.

Authors:  Noah F Fine Nathel; Lucas A Morrill; Herbert Mayr; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-08-09       Impact factor: 15.419

5.  Safety Assessment of Benzyne Generation from a Silyl Triflate Precursor.

Authors:  Andrew V Kelleghan; Carl A Busacca; Max Sarvestani; Ivan Volchkov; Jose M Medina; Neil K Garg
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

6.  Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.

Authors:  Jason V Chari; Francesca M Ippoliti; Neil K Garg
Journal:  J Org Chem       Date:  2019-03-06       Impact factor: 4.354

7.  Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions.

Authors:  Junhua Chen; Vignesh Palani; Thomas R Hoye
Journal:  J Am Chem Soc       Date:  2016-03-28       Impact factor: 15.419

8.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

9.  Nitrone Cycloadditions of 1,2-Cyclohexadiene.

Authors:  Joyann S Barber; Evan D Styduhar; Hung V Pham; Travis C McMahon; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-02-18       Impact factor: 15.419

10.  Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.

Authors:  Matthew S McVeigh; Andrew V Kelleghan; Michael M Yamano; Rachel R Knapp; Neil K Garg
Journal:  Org Lett       Date:  2020-05-21       Impact factor: 6.005

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