Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2323-2330
Author(s):  
Norio Sakai ◽  
Hiromu Maeda ◽  
Yohei Ogiwara
Keyword(s):  
Coupling Reaction ◽  
Sulfur Source ◽  
Diphenyl Diselenide ◽  
One Pot ◽  
Alkyl Aryl ◽  
One Pot Synthesis ◽  
Aryl Iodides ◽  
Alkyl Moiety ◽  
Aryl Sulfides ◽  
Three Component Coupling

A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.

scholarly journals Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

2013 ◽  
Vol 9 ◽  
pp. 467-475 ◽  
Author(s):  
Silvia M Soria-Castro ◽  
Alicia B Peñéñory
Keyword(s):  
Microwave Irradiation ◽  
Microwave Heating ◽  
Catalytic System ◽  
Low Cost ◽  
One Pot ◽  
Alkyl Aryl ◽  
One Pot Synthesis ◽  
Aryl Iodides ◽  
The One ◽  
Aryl Sulfides

S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100 °C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the “one-pot” synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.

A Facile One-Pot Synthesis of Alkyl Aryl Sulfides from Aryl Bromides

2004 ◽  
Vol 69 (9) ◽  
pp. 3236-3239 ◽  
Author(s):  
Jungyeob Ham ◽  
Inho Yang ◽  
Heonjoong Kang
Keyword(s):  
One Pot ◽  
Alkyl Aryl ◽  
One Pot Synthesis ◽  
Aryl Bromides ◽  
Aryl Sulfides

One-Pot Synthesis of Substituted Quinolines by Iridium-Catalyzed Three-Component Coupling Reaction.

ChemInform ◽  
2005 ◽  
Vol 36 (24) ◽  
Author(s):  
Takeyuki Igarashi ◽  
Takashi Inada ◽  
Tadao Sekioka ◽  
Takayuki Nakajima ◽  
Isao Shimizu
Keyword(s):  
Coupling Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Quinolines ◽  
Three Component Coupling

Two inorganic–organic hybrid silver-polyoxometalates as reusable catalysts for one-pot synthesis of propargylamines via a three-component coupling reaction at room temperature

CrystEngComm ◽  
2020 ◽  
Vol 22 (15) ◽  
pp. 2642-2648 ◽  
Author(s):  
Ming-Yu Dou ◽  
Xian-Qiang Huang ◽  
Guo-Yu Yang
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
One Pot ◽  
Catalytic Activities ◽  
Organic Hybrid ◽  
One Pot Synthesis ◽  
Three Component Coupling

Two silver-polyoxometalates [Ag3L2(DMSO)2][PW12O40]·4DMSO (1) and [(Ag2L2)2][SiW12O40]·10DMSO·2H2O (2) are made and 1 shows good catalytic activities for three-component coupling reaction.

One-pot Synthesis of Substituted Quinolines by Iridium-catalyzed Three-component Coupling Reaction

2005 ◽  
Vol 34 (1) ◽  
pp. 106-107 ◽  
Author(s):  
Takeyuki Igarashi ◽  
Takashi Inada ◽  
Tadao Sekioka ◽  
Takayuki Nakajima ◽  
Isao Shimizu
Keyword(s):  
Coupling Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Quinolines ◽  
Three Component Coupling
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