Literature DB >> 11674150

Synthesis of Secondary Amines via N-(Benzoyloxy)amines and Organoboranes.

O. Phanstiel1, Q. X. Wang, D. H. Powell, M. P. Ospina, B. A. Leeson.   

Abstract

A variety of primary amines (R-NH(2)) were converted to their corresponding N-(benzoyloxy)amines (i.e., R-NHOCOPh) under biphasic conditions in excellent yields (63-90%). The intermediate N-(benzoyloxy)amines were converted to their N-ethylamine derivatives upon reaction with triethylborane in THF in good yield (54-89%). These experiments demonstrated the similar chemistry of N-chloro- and N-(benzoyloxy)amines with organoboranes.

Entities:  

Year:  1999        PMID： 11674150     DOI： 10.1021/jo981613l

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


  5 in total

1.  Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.

Authors:  Aaron M Dumas; Gary A Molander; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors:  Scott N Mlynarski; Alexander S Karns; James P Morken
Journal:  J Am Chem Soc       Date:  2012-09-24       Impact factor: 15.419

3.  Scope and mechanism of intramolecular aziridination of cyclopent-3-enyl-methylamines to 1-azatricyclo[2.2.1.0(2,6)]heptanes with lead tetraacetate.

Authors:  Huayou Hu; Juan A Faraldos; Robert M Coates
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

4.  Pd-Catalyzed Alkene Diamination Reactions with O-Benzoylhydroxylamine Electrophiles: Evidence Supporting a Pd(II/IV) Catalytic Cycle, the Role of 2,4-Pentanedione Derivatives as Ligands, and Expanded Substrate Scope.

Authors:  Janelle K Kirsch; Gabriel A Gonzalez; Mason S Faculak; John P Wolfe
Journal:  J Org Chem       Date:  2021-08-04       Impact factor: 4.198

5.  An Improved PIII/PV═O-Catalyzed Reductive C-N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps.

Authors:  Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-03-25       Impact factor: 15.419
  5 in total

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