tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides

2021 ◽  
Author(s):  
Peng-Fei Dai ◽  
Yi-Ping Wang ◽  
Jian-Ping Qu ◽  
Yan-Biao Kang
Keyword(s):  
Tert Butyl ◽  
Dehydrogenative Coupling

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.

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 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.

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