Metal free oxidation of alkyl substituted aromatics with aqueous tert-butyl hydroperoxide under microwave irradiation

2009 ◽  
Vol 11 (11) ◽  
pp. 1857 ◽  
Author(s):  
Hao He ◽  
Bao-Jian Pei ◽  
Albert W. M. Lee
Keyword(s):  
Microwave Irradiation ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Free Oxidation

ChemInform Abstract: Metal-Free Csp3-N Bond Cleavage of Amides Using tert-Butyl Hydroperoxide as Oxidant.

ChemInform ◽  
2015 ◽  
Vol 46 (28) ◽  
pp. no-no ◽  
Author(s):  
Shengmei Guo ◽  
Zheng Zhu ◽  
Lin Lu ◽  
Wenbiao Zhang ◽  
Jiuhan Gong ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide

scholarly journals α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

2017 ◽  
Vol 13 ◽  
pp. 1079-1084 ◽  
Author(s):  
Liquan Tan ◽  
Cui Chen ◽  
Weibing Liu
Keyword(s):  
Oxidative Coupling ◽  
Optimum Conditions ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Radical Intermediates ◽  
Tert Butyl Hydroperoxide ◽  
Aryl Ketones

We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I2−tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several different reactions, which proceeded self-sequentially in a single reactor. A labeling experiment using 18O-labeled H2O confirmed that the oxygen in the product was derived from TBHP, not from H2O in the TBHP solvent.

Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source

2018 ◽  
Vol 16 (44) ◽  
pp. 8620-8628 ◽  
Author(s):  
Om P. S. Patel ◽  
Nitesh Kumar Nandwana ◽  
Ajay Kumar Sah ◽  
Anil Kumar
Keyword(s):  
Carbon Source ◽  
Dual Role ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide

A metal-free method is developed for the aminomethylation of imidazoheterocycles with 2/4-aminoheterocycles using TBHP as a carbon source as well as an oxidant.

TBHP/n-Bu4PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 136-140
Author(s):  
Mehdi Adib ◽  
Rahim Pashazadeh
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Catalytic Amount ◽  
Facile Synthesis ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Dehydrogenative Coupling ◽  
Tert Butyl Hydroperoxide ◽  
Methylene Groups

A transition-metal-free oxidative cross-dehydrogenative coupling reaction has been developed for the preparation of symmetrical carboxylic anhydrides through self-coupling dual C–O bond formations of aryl methanols. In the presence of a catalytic amount of tetrabutylphosphonium bromide (TBPB) as transfer agent and aqueous tert-butyl hydroperoxide (TBHP) as oxidant and reactant, methylene groups of aryl methanols were efficiently oxidized to C=O and coupled with the peroxide oxygen from TBHP to form a diverse array of symmetrical carboxylic anhydride derivatives.

A Metal-Free Synthesis of 3-Phenoxyimidazo Heterocycles by Catalytic Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3169-3176 ◽  
Author(s):  
Li Zhao ◽  
Jian Zhang ◽  
Guofu Zhong ◽  
Yizhou Chen ◽  
Shanlu Wang ◽  
...  
Keyword(s):  
Oxidative Cyclization ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Air Atmosphere ◽  
Tert Butyl Hydroperoxide ◽  
Lignin Model

A metal-free catalytic oxidative cyclization of 2-aminopyridines and 2-aminobenzothiazole with lignin model 2-phenoxyacetophenones was developed, in which inexpensive iodine was used as the catalyst and tert-butyl hydroperoxide (TBHP) was the oxidant. The reaction proceeded smoothly under an air atmosphere to produce valuable 3-phenoxyimidazo[1,2-a]pyridines and 3-phenoxybenzo[d]imidazo[2,1-b]thiazoles, respectively, in moderate to good yields.

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