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Tuning Inner-Sphere Electron Transfer in a Series of Copper/Nitrosoarene Adducts.

Author(s): Askari MS, Effaty F, Gennarini F, Orio M, Le Poul N, Ottenwaelder X

Inorg Chem. 2020 Feb 19;: Authors: Askari MS, Effaty F, Gennarini F, Orio M, Le Poul N, Ottenwaelder X

Article GUID: 32073833
A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.

Author(s): Huang Z, Askari MS, Esguerra KVN, Dai TY, Kwon O, Ottenwaelder X, Lumb JP

Chem Sci. 2016 Jan 01;7(1):358-369 Authors: Huang Z, Askari MS, Esguerra KVN, Dai TY, Kwon O, Ottenwaelder X, Lumb JP

Article GUID: 29861988
Synthesis of Highly Functionalized Triarylbismuthines by Functional Group Manipulation and Use in Palladium- and Copper-Catalyzed Arylation Reactions.

Author(s): Hébert M, Petiot P, Benoit E, Dansereau J, Ahmad T, Le Roch A, Ottenwaelder X, Gagnon A

J Org Chem. 2016 07 01;81(13):5401-16 Authors: Hébert M, Petiot P, Benoit E, Dansereau J, Ahmad T, Le Roch A, Ottenwaelder X, Gagnon A

Article GUID: 27231755
Supramolecular control of monooxygenase reactivity in a copper(ii) cryptate.

Author(s): Chaloner L, Khomutovskaya A, Thomas F, Ottenwaelder X

Dalton Trans. 2016 Jul 05;45(27):11109-19 Authors: Chaloner L, Khomutovskaya A, Thomas F, Ottenwaelder X

Article GUID: 27328176
Title:A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.
Authors:Huang Z,  Askari MS,  Esguerra KVN,  Dai TY,  Kwon O,  Ottenwaelder X,  Lumb JP
Link:https://www.ncbi.nlm.nih.gov/pubmed/29861988?dopt=Abstract
DOI:10.1039/c5sc02395e
Category:Chem Sci
PMID:29861988
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]