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

Synthesis ◽  
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.

Metal-Free Ammonium Iodide Catalyzed Oxidative Dehydrocoupling of Silanes with Alcohols

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1620-1623 ◽  
Author(s):  
Pailla Kumar ◽  
Sheng-rong Guo ◽  
Yan-qin Yuan
Keyword(s):  
Transition Metal ◽  
Oxidative Coupling ◽  
Ammonium Iodide ◽  
Reaction Conditions ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Free Ammonium

An ammonium iodide catalyzed direct oxidative coupling of silanes with alcohols to give various alkoxysilane derivatives was discovered. tert-Butyl hydroperoxide proved to be an efficient oxidant for this transformation. Attractive features of this protocol include its transition-metal-free nature and the mild reaction conditions.

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.

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

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.

An Efficient Ultrasonic-Assisted Synthesis of Enol Carbamates via Oxidative Coupling of Formamides with 1,3-Dicarbonyl Compounds

2020 ◽  
Vol 17 (7) ◽  
pp. 507-511
Author(s):  
Jafar Akbari ◽  
Alireza Akbari Meyestani
Keyword(s):  
Oxidative Coupling ◽  
Cuo Nanoparticles ◽  
Reaction Conditions ◽  
Dicarbonyl Compounds ◽  
Butyl Hydroperoxide ◽  
Mild Conditions ◽  
Tert Butyl Hydroperoxide ◽  
Ultrasonic Assisted ◽  
High Yields ◽  
Derivatives Of

Sonochemical oxidative-coupling of formamides with 1,3-dicarbonyl compounds in the corresponding carbamates by CuO nanoparticles as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant has been reported. Various derivatives of enol carbamates were synthesized with good to high yields under the optimized reaction conditions. Compared with conventional methods, the main advantage of this method is mild conditions.

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