Literature DB >> 28323428

Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides.

Arijit A Adhikari1, Tamie Suzuki1, Reesheda T Gilbert1, Matthew R Linaburg1, John D Chisholm1.   

Abstract

The rearrangement of allylic trichloroacetimidates is a well-known transformation, but the corresponding rearrangement of benzylic trichloroacetimidates has not been explored as a method for the synthesis of benzylic amines. Conditions that provide the trichloroacetamide product from a benzylic trichloroacetimidate in high yield have been developed. Methods were also investigated to transform the trichloroacetamide product directly into the corresponding amine, carbamate, and urea. A cationic mechanism for the rearrangement is implicated by the available data.

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Year:  2017        PMID： 28323428      PMCID： PMC5458781          DOI： 10.1021/acs.joc.7b00245

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


  27 in total

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6.  Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction.

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8.  Stereoselective rearrangement of trichloroacetimidates: application to the synthesis of alpha-glycosyl ureas.

Authors:  Nathaniel H Park; Hien M Nguyen
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

9.  Palladium(II)-catalyzed rearrangement of glycal trichloroacetimidates: application to the stereoselective synthesis of glycosyl ureas.

Authors:  Gregory J Mercer; Jaemoon Yang; Matthew J McKay; Hien M Nguyen
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  7 in total

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2.  Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

Authors:  Nivedita S Mahajani; Rowan I L Meador; Tomas J Smith; Sarah E Canarelli; Arijit A Adhikari; Jigisha P Shah; Christopher M Russo; Daniel R Wallach; Kyle T Howard; Alexandra M Millimaci; John D Chisholm
Journal:  J Org Chem       Date:  2019-05-30       Impact factor: 4.354

3.  Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Authors:  Jonathan J Kennedy-Ellis; Erik D Boldt; Sherry R Chemler
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4.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

5.  Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Authors:  Nivedita S Mahajani; John D Chisholm
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6.  Synthesis of 1,1'-Diarylethanes and Related Systems by Displacement of Trichloroacetimidates with Trimethylaluminum.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  J Org Chem       Date:  2018-03-08       Impact factor: 4.354

7.  Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

Authors:  Tamie Suzuki; Nilamber A Mate; Arijit A Adhikari; John D Chisholm
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  7 in total

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