PERFORM Publications

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Title		Authors	PubMed ID
1	A high-fidelity simulator for evaluation of hemodynamic response during cardiopulmonary resuscitation in hypogravity environments	Lord Z; Andrade C; Leroux L; Kadem L;	41741473 CHEMISTRY
2	Transcriptomic analysis suggests the inhibition of DNA damage repair in green alga Raphidocelis subcapitata exposed to roxithromycin.	Guo J, Bai Y, Chen Z, Mo J, Li Q, Sun H, Zhang Q	32505758 CHEMISTRY
3	Four Aromatic Intradiol Ring Cleavage Dioxygenases from Aspergillus niger.	Semana P, Powlowski J	31540981 CHEMISTRY
4	How Well Does the Hole-Burning Action Spectrum Represent the Site-Distribution Function of the Lowest-Energy State in Photosynthetic Pigment-Protein Complexes?	Zazubovich V, Jankowiak R	31265294 CHEMISTRY
5	Virtual screening, docking, and dynamics of potential new inhibitors of dihydrofolate reductase from Yersinia pestis.	Bastos Lda C, de Souza FR, Guimarães AP, Sirouspour M, Cuya Guizado TR, Forgione P, Ramalho TC, França TC	26494420 CHEMISTRY
6	Docking and molecular dynamics studies of peripheral site ligand-oximes as reactivators of sarin-inhibited human acetylcholinesterase.	de Almeida JS, Cuya Guizado TR, Guimarães AP, Ramalho TC, Gonçalves AS, de Koning MC, França TC	26612005 CHEMISTRY
7	O(6)-Alkylguanine DNA Alkyltransferase Repair Activity Towards Intrastrand Cross-Linked DNA is Influenced by the Internucleotide Linkage.	O'Flaherty DK, Wilds CJ	26692563 CHEMISTRY
8	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
9	The Chemical Ecology of Predatory Soil Bacteria.	Findlay BL	27035738 CHEMISTRY
10	Mechanistic studies of new oximes reactivators of human butyryl cholinesterase inhibited by cyclosarin and sarin.	de Lima WE, Francisco A, da Cunha EF, Radic Z, Taylor P, França TC, Ramalho TC	27125569 CHEMISTRY

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
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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