scholarly journals Cross-Dehydrogenative coupling reaction and arylation of quinoxalin-2(1H)-ones under iodide/peroxide system condition

SynOpen ◽  
2021 ◽  
Author(s):  
Yujuan Wu ◽  
Xianglong Chu ◽  
Di Yang ◽  
chen ma ◽  
Caixia Xie
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Simple Method ◽  
Metal Free ◽  
Radical Initiator ◽  
Dehydrogenative Coupling ◽  
One Step

A simple method has been developed for the synthesis of 3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-one and 3-aryl-quinoxalin-2(1H)-one derivatives through C-H activation of quinoxalin-2(1H)-ones by peroxides and iodide. In this protocol, the peroxide (TBPB) serves as both the radical initiator and aryl source, realizing arylation of quinoxalin-2(1H)-one in a one-step reaction. The methodology has the advantages of being a metal-free strategy and having broad functional group tolerance.

Metal-free cross-coupling reaction of aldehydes with disulfides by using DTBP as an oxidant under solvent-free conditions

2014 ◽  
Vol 16 (5) ◽  
pp. 2644-2652 ◽  
Author(s):  
Jing-Wen Zeng ◽  
Yi-Chen Liu ◽  
Ping-An Hsieh ◽  
Yu-Ting Huang ◽  
Chih-Lun Yi ◽  
...  
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Solvent Free ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
Solvent Free Conditions

A DTBP-promoted C–H thiolation of aldehydes with disulfides under metal-free and solvent-free conditions is described. The system shows good functional group tolerance to afford thioesters in moderate to excellent yields.

(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

Metal-free catalyzed arylsulfonylation of chloroquinoline with sodium arylsulfinates under microwave irradiation

2018 ◽  
Vol 73 (5) ◽  
pp. 295-303 ◽  
Author(s):  
Xi-Yong Li ◽  
Ya-Min Sun ◽  
Jin-Wei Yuan
Keyword(s):  
Microwave Irradiation ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
Wide Range

AbstractAn efficient protocol for the synthesis of 2-arylsulfonyl quinolines has been developed via a metal-free catalyzed cross-coupling reaction of chloroquinoline with sodium arylsulfinates in moderate-to-good yields under microwave irradiation. The reactions proceed with a wide range of substrates with good functional group tolerance.

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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