Amide bond synthesis via silver(I) N-heterocyclic carbene-catalyzed and tert-butyl hydroperoxide-mediated oxidative coupling of alcohols with amines under base free conditions

2019 ◽  
Vol 60 (12) ◽  
pp. 847-851 ◽  
Author(s):  
Ramesh Balaboina ◽  
Narasimha Swamy Thirukovela ◽  
Ravinder Vadde ◽  
Chandra Sekhar Vasam
Keyword(s):  
Oxidative Coupling ◽  
Amide Bond ◽  
Butyl Hydroperoxide ◽  
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 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.

C(sp3)–H Bond Functionalization of Alcohols, Ketones, Nitriles, Ethers and Amides using tert-Butyl Hydroperoxide as a Radical Initiator

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 23-29
Author(s):  
Nai-Xing Wang ◽  
Yalan Xing ◽  
Lei-Yang Zhang ◽  
Yue-Hua Wu
Keyword(s):  
Organic Synthesis ◽  
Oxidative Coupling ◽  
Recent Progress ◽  
Organic Molecules ◽  
Bond Functionalization ◽  
Butyl Hydroperoxide ◽  
Radical Initiator ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Unsaturated Carboxylic Acids

The C(sp3)–H bond is found widely in organic molecules. Recently, the functionalization of C(sp3)–H bonds has developed into a powerful tool for augmenting highly functionalized frameworks in organic synthesis. Based on the results obtained in our group, the present account mainly summarizes recent progress on the functionalization of C(sp3)–H bonds of aliphatic alcohols, ketones, alkyl nitriles, and ethers with styrene or cinnamic acid using tert-butyl hydroperoxide (TBHP) as a radical initiator.1 Introduction2 Oxidative Coupling of Styrenes with C(sp3)–H Bonds3 Decarboxylative Cross-Couplings of α,β-Unsaturated Carboxylic Acids with C(sp3)–H Bonds4 Conclusions

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.

Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant

2012 ◽  
Vol 14 (13) ◽  
pp. 3384-3387 ◽  
Author(s):  
Erbo Shi ◽  
Ying Shao ◽  
Shulin Chen ◽  
Huayou Hu ◽  
Zhaojun Liu ◽  
...  
Keyword(s):  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Tetrabutylammonium Iodide
Sign in / Sign up

Export Citation Format

Share Document