Di-tert-butyl peroxide (DTBP) promoted dehydrogenative coupling: an expedient and metal-free synthesis of oxindoles via intramolecular C(sp2)–H and C(sp3)–H bond activation

RSC Advances ◽  
2015 ◽  
Vol 5 (85) ◽  
pp. 69119-69123 ◽  
Author(s):  
Biplab Mondal ◽  
Brindaban Roy
Keyword(s):  
Bond Activation ◽  
Metal Free ◽  
Tert Butyl ◽  
Dehydrogenative Coupling ◽  
Butyl Peroxide

An efficient di-tert-butyl peroxide (DTBP) promoted synthesis of oxindole has been developed. This methodology involves C(sp3)–H and C(sp2)–H bond activation under metal-free conditions.

Metal-free S-methylation of diaryl disulfides with di-tert-butyl peroxide

2018 ◽  
Vol 59 (13) ◽  
pp. 1240-1243 ◽  
Author(s):  
Xiangmei Wu ◽  
Yan Wang
Keyword(s):  
Metal Free ◽  
Tert Butyl ◽  
Butyl Peroxide

scholarly journals Oxidative cross-dehydrogenative coupling (CDC) via C(sp2)–H bond functionalization: tert-butyl peroxybenzoate (TBPB)-promoted regioselective direct C-3 acylation/benzoylation of 2H-indazoles with aldehydes/benzyl alcohols/styrenes

RSC Advances ◽  
2021 ◽  
Vol 11 (23) ◽  
pp. 14178-14192
Author(s):  
Richa Sharma ◽  
Lalit Yadav ◽  
Ravi Kant Yadav ◽  
Sandeep Chaudhary
Keyword(s):  
Transition Metal ◽  
Benzyl Alcohols ◽  
Bond Functionalization ◽  
Metal Free ◽  
Tert Butyl ◽  
Dehydrogenative Coupling

An efficient transition-metal-free oxidative C(sp2)–H/C(sp2)–H cross-dehydrogenative coupling via C(sp2)–H bond functionalization for regioselective C-3 acylation/benzoylation of 2H-indazoles with aldehydes/benzyl alcohols/styrenes is reported.

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.

scholarly journals Metal-Free Preparation of Cycloalkyl Aryl SulfidesviaDi-tert-butyl Peroxide-Promoted Oxidative C(sp3)H Bond Thiolation of Cycloalkanes

2014 ◽  
Vol 356 (11-12) ◽  
pp. 2719-2724 ◽  
Author(s):  
Jincan Zhao ◽  
Hong Fang ◽  
Jianlin Han ◽  
Yi Pan ◽  
Guigen Li
Keyword(s):  
Metal Free ◽  
Tert Butyl ◽  
Butyl Peroxide

Metal-Free Synthesis of α-Aminophosphonates from Tertiary Amines and P(O)H Compounds via a Cross-Dehydrogenative Coupling Reaction

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2697-2700 ◽  
Author(s):  
Guo Tang ◽  
Binzhou Lin ◽  
Guozhang Lu ◽  
Rongcan Lin ◽  
Yiqun Cui ◽  
...  
Keyword(s):  
Tertiary Amine ◽  
Coupling Reaction ◽  
Transition Metal Catalysts ◽  
Tertiary Amines ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Dehydrogenative Coupling ◽  
Tert Butyl Hydroperoxide ◽  
Aromatic And Aliphatic Amines

The various α-aminophosphonates have been prepared from tertiary aromatic and aliphatic amines with P(O)H compounds via a tert-butyl hydroperoxide mediated cross-dehydrogenative coupling reaction, eliminating the need for transition-metal catalysts. The oxidation of tertiary amine by tert-butyl hydroperoxide generates an iminium cation intermediate. A further addition of P(O)H compound to iminium cation gives the desired product.

scholarly journals Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)–H bonds

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Fufang Wu ◽  
Xuanzhen Han ◽  
Xuejian Li ◽  
Xiaobao Shen ◽  
Chang Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Coupling Reactions ◽  
Chemical Bonds ◽  
Reaction Conditions ◽  
Transition Metal Catalyst ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Ether Oxygen

AbstractCross-dehydrogenative coupling reactions provide a method to construct new chemical bonds by direct C–H activation without any pre-functionalization. Compared to functionalization of a C–H bond α- to ether oxygen, α- to carbonyl, or at a benzylic position, functionalization of unactivated hydrocarbons is difficult and often requires high temperatures, a transition-metal catalyst, or a superstoichiometric quantity of volatile, toxic, and explosive tert-butylhydroperoxide. Here, a cross-dehydrogenative C–O coupling reaction of N-hydroxyphthalimide with unactivated alkanes, nitriles, ethers, and thioethers has been realized by using iodobenzene diacetate as the radical initiator. The current protocol enables efficient functionalization of unactivated hydrocarbons and nitriles through inert C(sp3)–H bond activation under mild reaction conditions. O-substituted NHPI derivatives are generated in good yields under metal-free conditions.

Fundamental Thermal Hazard Investigation for Tert-Butyl Peroxide Reactor Using DSC and TGA Techniques

2011 ◽  
Vol 21 (1) ◽  
pp. 53-63 ◽  
Author(s):  
Chien-Jung Chen ◽  
Jen-Hao Chi ◽  
Sheng-Hung Wu ◽  
Cheng-Tung Chen ◽  
Hsiu-Fen Tsai
Keyword(s):  
Thermal Hazard ◽  
Tert Butyl ◽  
Butyl Peroxide
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