Literature DB >> 22900473

α-Aminoxylation of ketones and β-chloro-α-aminoxylation of enones with TEMPO and chlorocatecholborane.

Yi Li1, Martin Pouliot, Thomas Vogler, Philippe Renaud, Armido Studer.   

Abstract

Oxidation of various cyclic and acyclic ketones under mild conditions with chlorocatecholborane, a bulky pyridine base, and TEMPO to the corresponding α-aminoxylated products in good to excellent yields (52-99%) is described. For enones as substrates, products of a β-chloro-α-aminoxylation are obtained (70-89%).

Entities:  

Year:  2012        PMID： 22900473     DOI： 10.1021/ol301979b

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


  5 in total

1.  Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.

Authors:  Juno C Siu; Joseph B Parry; Song Lin
Journal:  J Am Chem Soc       Date:  2019-01-28       Impact factor: 15.419

2.  Interception of 1,2-cyclohexadiene with TEMPO radical.

Authors:  Matthew S McVeigh; Neil K Garg
Journal:  Tetrahedron Lett       Date:  2021-11-15       Impact factor: 2.415

3.  Hydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms.

Authors:  Alexandre Pinto; Daniel Kaiser; Boris Maryasin; Giovanni Di Mauro; Leticia González; Nuno Maulide
Journal:  Chemistry       Date:  2018-01-24       Impact factor: 5.236

4.  Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO.

Authors:  Xiaoming Jie; Yaping Shang; Zhe-Ning Chen; Xiaofeng Zhang; Wei Zhuang; Weiping Su
Journal:  Nat Commun       Date:  2018-11-27       Impact factor: 14.919

5.  A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones.

Authors:  Tsukasa Tanaka; Takehiro Kiuchi; Yuuki Ooe; Hajime Iwamoto; Shin-Ya Takizawa; Shigeru Murata; Eietsu Hasegawa
Journal:  ACS Omega       Date:  2022-01-26
  5 in total

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