Allylic C–H Activations Using Cu(II) 2-Quinoxalinol Salen and tert-Butyl Hydroperoxide

Using a Cu(II) 2-quinoxalinol salen complex as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, allylic activations of olefin substrates can be converted to the corresponding enones or 1,4-enediones. Excellent yields can be achieved (up to 99%) within a very short reaction time and w...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-05, Vol.77 (10), p.4628-4633
Main Authors: Li, Yuancheng, Lee, Tae Bum, Wang, Tanyu, Gamble, Audrey V, Gorden, Anne E. V
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Using a Cu(II) 2-quinoxalinol salen complex as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, allylic activations of olefin substrates can be converted to the corresponding enones or 1,4-enediones. Excellent yields can be achieved (up to 99%) within a very short reaction time and with great tolerance for additional functional groups. Possible mechanistic pathways have been characterized using Raman spectroscopy, cyclic voltammetry, and theoretical calculations.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300372q