Literature DB >> 23441814

Palladium-catalyzed synthesis of N-aryl carbamates.

Ekaterina V Vinogradova1, Nathaniel H Park, Brett P Fors, Stephen L Buchwald.   

Abstract

An efficient synthesis of aryl carbamates was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of ArX (X = Cl, OTf) with sodium cyanate. The use of aryl triflates as electrophilic components in this transformation allowed for an expanded substrate scope for direct synthesis of aryl isocyanates. This methodology provides direct access to major carbamate protecting groups, S-thiocarbamates, and diisocyanate precursors to polyurethane materials.

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Year:  2013        PMID: 23441814      PMCID: PMC3685193          DOI: 10.1021/ol400369n

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


  11 in total

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3.  Palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate: a practical synthesis of unsymmetrical ureas.

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Journal:  J Am Chem Soc       Date:  2012-06-29       Impact factor: 15.419

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6.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
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8.  Catalytic aza-Wittig cyclizations for heteroaromatic synthesis.

Authors:  Stephen P Marsden; Alison E McGonagle; Ben McKeever-Abbas
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9.  Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: merging organic and transition metal catalysis.

Authors:  Bradley G Jellerichs; Jong-Rock Kong; Michael J Krische
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10.  Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

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  1 in total

1.  Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis.

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Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

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