Literature DB >> 24410270

Enabling the use of heterocyclic arynes in chemical synthesis.

Adam E Goetz, Neil K Garg.   

Abstract

Heterocyclic arynes have long been targeted as potential tools for the synthesis of substituted heterocycles. Recent advances have led to an improved understanding of the factors that determine regioselectivity in reactions of these strained intermediates and, in turn, the aryne distortion model. This paper highlights the use of this predictive model to enable the use of heterocyclic arynes, such as indolynes and pyridynes, in chemical synthesis.

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Year:  2014        PMID: 24410270     DOI: 10.1021/jo402723e

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  24 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.  Cycloadditions of Oxacyclic Allenes and a Catalytic Asymmetric Entryway to Enantioenriched Cyclic Allenes.

Authors:  Michael M Yamano; Rachel R Knapp; Aurapat Ngamnithiporn; Melissa Ramirez; Kendall N Houk; Brian M Stoltz; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-20       Impact factor: 15.336

3.  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

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.  Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C-H silylation of phenols with traceless acetal directing groups.

Authors:  Parham Asgari; Udaya Sree Dakarapu; Hiep H Nguyen; Junha Jeon
Journal:  Tetrahedron       Date:  2016-12-08       Impact factor: 2.457

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.  Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Authors:  Travis C McMahon; Jose M Medina; Yun-Fang Yang; Bryan J Simmons; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2015-03-20       Impact factor: 15.419

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