Scalable electrochemical oxidant-and metal-free dehydrogenative coupling of S–H/N–H

2019 ◽  
Vol 17 (6) ◽  
pp. 1370-1374 ◽  
Author(s):  
Shanyu Tang ◽  
Yan Liu ◽  
Longjia Li ◽  
Xuanhe Ren ◽  
Jiao Li ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Metal Free ◽  
Dehydrogenative Coupling

The synthesis of sulfenamides via the oxidant- and metal-free electrochemical dehydrogenative coupling reaction of thiols and amines.

(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)–H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2432-2436 ◽  
Author(s):  
Can Jin ◽  
Weike Su ◽  
Bin Sun ◽  
Zhiyang Yan
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Metal Free ◽  
Alternative Method ◽  
Dehydrogenative Coupling ◽  
Wide Range ◽  
Ready Access

A novel PhI(OAc)2-mediated cross-dehydrogenative coupling reaction of α-C(sp3)–H bonds adjacent to a hetero atom with various azoles has been developed, which provides an alternative method for constructing C–N bonds with high atom efficiency. This new protocol requires no metal catalyst and it provides ready access to a wide range of N-alkylated azole derivatives in moderate to excellent yields by using commercially available PhI(OAc)2 as the sole oxidant. Furthermore, the method is effective on a gram scale, which highlights the practicality of this transformation. The result of radical-captured experiments indicated that the transformation might involve a free-radical pathway.

Regioselective transition metal-free acylation of coumarins via cross-dehydrogenative coupling reaction of coumarins and aldehydes

2016 ◽  
Vol 57 (33) ◽  
pp. 3701-3705 ◽  
Author(s):  
Mehdi Adib ◽  
Saideh Rajai-Daryasarei ◽  
Rahim Pashazadeh ◽  
Mahnaz Tajik ◽  
Peiman Mirzaei
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Free ◽  
Dehydrogenative Coupling

A Metal-Free Cross-Dehydrogenative Coupling Reaction of Amides to Access N-Alkylazoles

Synlett ◽  
2016 ◽  
Vol 27 (19) ◽  
pp. 2705-2708 ◽  
Author(s):  
Shengmei Guo ◽  
Hu Cai ◽  
Zheng Zhu ◽  
Yufeng Wang ◽  
Mingmeng Yang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Metal Free ◽  
Dehydrogenative Coupling

Transition Metal-Free Cross-Dehydrogenative Coupling Reaction of Coumarins with Acetonitrile or Acetone

2018 ◽  
Vol 83 (21) ◽  
pp. 13030-13035 ◽  
Author(s):  
Rongxing Zhang ◽  
Shengzhou Jin ◽  
Qian Liu ◽  
Sen Lin ◽  
Zhaohua Yan
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Free ◽  
Dehydrogenative Coupling

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.

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