Keyword search (4,163 papers available)

"Ottenwaelder X" 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 Mechanochemistry for Metal-Organic Frameworks and Covalent-Organic Frameworks (MOFs, COFs): Methods, Materials, and Mechanisms Marrett JM; Effaty F; Ottenwaelder X; Frišcic T; 40708349
CHEMBIOCHEM
3 Mechanochemical Synthesis of Boroxine-linked Covalent Organic Frameworks Hamzehpoor E; Effaty F; Borchers TH; Stein RS; Wahrhaftig-Lewis A; Ottenwaelder X; Frišcic T; Perepichka DF; 38970305
CHEMBIOCHEM
4 Cooperative Sensitization Upconversion in Solution Dispersions of Co-Crystal Assemblies of Mononuclear Yb3+ and Eu3+ Complexes Sun G; Xie Y; Wang Y; Mandl GA; Maurizio SL; Zhang H; Ottenwaelder X; Capobianco JA; Sun L; 37040148
CNSR
5 Resonant acoustic mixing (RAM) for efficient mechanoredox catalysis without grinding or impact media Effaty F; Gonnet L; Koenig SG; Nagapudi K; Ottenwaelder X; Frišcic T; 36546478
CHEMBIOCHEM
6 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
7 Programmed Synthesis of Tetra-Aryl Thiophenes with Stepwise, Ester-Controlled Regioselectivity Messina C; Ottenwaelder X; Forgione P; 34506149
CHEMBIOCHEM
8 Five Nitrogen Oxidation States from Nitro to Amine: Stabilization and Reactivity of a Metastable Arylhydroxylamine Complex. Zsombor-Pindera J; Effaty F; Escomel L; Patrick B; Kennepohl P; Ottenwaelder X; 33124796
CHEMBIOCHEM
9 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
10 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
11 Synthesis of Highly Functionalized Triarylbismuthines by Functional Group Manipulation and Use in Palladium- and Copper-Catalyzed Arylation Reactions. Hébert M, Petiot P, Benoit E, Dansereau J, Ahmad T, Le Roch A, Ottenwaelder X, Gagnon A 27231755
CHEMBIOCHEM
12 Supramolecular control of monooxygenase reactivity in a copper(ii) cryptate. Chaloner L, Khomutovskaya A, Thomas F, Ottenwaelder X 27328176
CHEMBIOCHEM

 

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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