Keyword search (4,164 papers available)

"Askari MS" Authored Publications:

Title Authors PubMed ID
1 Overlap and Covalency in a κN-Arylnitrosyl Cu(II) Metalloradical Formed by Hydroxylamine Oxidative Binding MacKay A; Zsombor-Pindera J; Effaty F; Sheibany N; Gennarini F; Habibian M; Chen F; Askari MS; Brytskyi M; Kroeker S; Kennepohl P; Ottenwaelder X; 41524899
CHEMBIOCHEM
2 Sterically-Hindered Molecular p-Dopants Promote Integer Charge Transfer in Organic Semiconductors Charoughchi S; Liu JT; Berteau-Rainville M; Hase H; Askari MS; Bhagat S; Forgione P; Salzmann I; 37220083
CHEMBIOCHEM
3 Intramolecular H-bond stabilization of a primary hydroxylamine in salen-type metal complexes Singh H; MacKay A; Sheibany N; Chen F; Mosser M; Rouet PÉ; Rousseau F; Askari MS; Ottenwaelder X; 34545379
CHEMBIOCHEM
4 Tuning Inner-Sphere Electron Transfer in a Series of Copper/Nitrosoarene Adducts. Askari MS, Effaty F, Gennarini F, Orio M, Le Poul N, Ottenwaelder X 32073833
CHEMBIOCHEM
5 Facile Aqueous-Phase Synthesis of an Ultrasmall Bismuth Nanocatalyst for the Reduction of 4-Nitrophenol. Liang Y, Manioudakis J, Macairan JR, Askari MS, Forgione P, Naccache R 31552336
CHEMBIOCHEM
6 A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols. Huang Z, Askari MS, Esguerra KVN, Dai TY, Kwon O, Ottenwaelder X, Lumb JP 29861988
CHEMISTRY

 

Title:A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.
Authors:Huang ZAskari MSEsguerra KVNDai TYKwon OOttenwaelder XLumb JP
Link:https://www.ncbi.nlm.nih.gov/pubmed/29861988?dopt=Abstract
DOI:10.1039/c5sc02395e
Publication:Chemical science
Keywords:
PMID:29861988 Category:Chem Sci Date Added:2019-06-20
Dept Affiliation: CHEMISTRY
1 Department of Chemistry , McGill University , Montreal , QC H3A 0B8 , Canada . Email: jean-philip.lumb@mcgill.ca.
2 Department of Chemistry and Biochemistry , Concordia University , Montreal , QC H4B 1R6 , Canada . Email: dr.x@concordia.ca.

Description:

A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.

Chem Sci. 2016 Jan 01;7(1):358-369

Authors: Huang Z, Askari MS, Esguerra KVN, Dai TY, Kwon O, Ottenwaelder X, Lumb JP

Abstract

Nitrogen-containing heterocycles are fundamentally important to the function of pharmaceuticals, agrochemicals and materials. Herein, we report a bio-inspired approach to the synthesis of oxindoles, which couples the energetic requirements of dehydrogenative C-N bond formation to the reduction of molecular oxygen (O2). Our method is inspired by the biosynthesis of melanin pigments (melanogenesis), but diverges from the biosynthetic polymerization. Mechanistic analysis reveals the involvement of CuII-semiquinone radical intermediates, which enable dehydrogenative carbon-heteroatom bond formation that avoids a catechol/quinone redox couple. This mitagates the deleterious polarity reversal that results from phenolic dearomatization, and enables a high-yielding phenolic C-H functionalization under catalytic aerobic conditions. Our work highlights the broad synthetic utility and efficiency of forming C-N bonds via a catalytic aerobic dearomatization of phenols, which is currently an underdeveloped transformation.

PMID: 29861988 [PubMed]





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