ChemInform Abstract: Metal-Free Deprotection of Terminal Acetonides by Using tert-Butyl Hydroperoxide in Aqueous Medium.

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.

Download Full-text

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

Organic & Biomolecular Chemistry ◽

10.1039/c8ob02432d ◽

2018 ◽

Vol 16 (44) ◽

pp. 8620-8628 ◽

Cited By ~ 12

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.

Download Full-text

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

Synlett ◽

10.1055/s-0036-1590905 ◽

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.

Download Full-text

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

Synthesis ◽

10.1055/s-0037-1610139 ◽

2018 ◽

Vol 50 (16) ◽

pp. 3169-3176 ◽

Cited By ~ 5

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.

Download Full-text

Synthesis of N -Sulfonylformamidines by tert -butyl Hydroperoxide–Promoted, metal-free, direct oxidative dehydrogenation of aliphatic amines

Tetrahedron ◽

10.1016/j.tet.2018.03.074 ◽

2018 ◽

Vol 74 (20) ◽

pp. 2475-2481 ◽

Cited By ~ 7

Author(s):

Ayijiamali Rouzi ◽

Ruzeahong Hudabaierdi ◽

Abudureheman Wusiman

Keyword(s):

Oxidative Dehydrogenation ◽

Aliphatic Amines ◽

Butyl Hydroperoxide ◽

Metal Free ◽

Tert Butyl ◽

Tert Butyl Hydroperoxide

Download Full-text

Metal-Free Oxidative Coupling of Tetrahydroisoquinolines and 3-Fluorooxindoles on Water

Synthesis ◽

10.1055/s-0039-1690213 ◽

2019 ◽

Vol 52 (03) ◽

pp. 471-478

Author(s):

Jian Ji ◽

Ling-Yan Chen ◽

Zi-Bin Qiu ◽

Xinfeng Ren ◽

Ya Li

Keyword(s):

Oxidative Coupling ◽

Reaction Conditions ◽

Butyl Hydroperoxide ◽

Metal Free ◽

Tert Butyl ◽

Tert Butyl Hydroperoxide

An efficient, metal-free oxidative coupling of tetrahydroisoquinolines and 3-fluorooxindoles on water has been developed. Using aqueous tert-butyl hydroperoxide as the oxidant, Et3N as the base, and water as the sole solvent, a variety of 3-fluorooxindoles fully substituted at the 3-position and containing a tetrahydroisoquinoline fragment has been successfully prepared in yields of up to 93% with an anti/syn stereoselectivity of up to 99:1 under very mild and safe reaction conditions.

Download Full-text