Literature DB >> 19178159

Indolynes as electrophilic indole surrogates: fundamental reactivity and synthetic applications.

Sarah M Bronner1, Kevin B Bahnck, Neil K Garg.   

Abstract

A mild method to access a variety of substituted indole derivatives has been developed. The strategy relies on the generation of highly reactive indolyne intermediates, which function as electrophilic indole surrogates.

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Year:  2009        PMID： 19178159     DOI： 10.1021/ol802958a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  25 in total

1.  An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Authors:  Adam E Goetz; Sarah M Bronner; Jordan D Cisneros; Joshua M Melamed; Robert S Paton; K N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-03       Impact factor: 15.336

2.  New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development.

Authors:  Neil Brown; Diheng Luo; Joseph A Decapo; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-12-23       Impact factor: 2.415

3.  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

4.  Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors:  Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

5.  Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Evan D Styduhar; Alexander D Huters; Nicholas A Weires; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

6.  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

7.  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

8.  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

9.  Experimental and theoretical investigations into the unusual regioselectivity of 4,5-, 5,6-, and 6,7-indole aryne cycloadditions.

Authors:  Ashley N Garr; Diheng Luo; Neil Brown; Christopher J Cramer; Keith R Buszek; David VanderVelde
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

10.  Indolyne and aryne distortions and nucleophilic regioselectivites.

Authors:  Paul H-Y Cheong; Robert S Paton; Sarah M Bronner; G-Yoon J Im; Neil K Garg; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419
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