- Synthesis of Aryl Dithiocarbamates from Tetramethylthiuram Monosulfide (TMTM) and Aryl Boronic Acids: Copper-Catalyzed Construction of C(sp2)-S Bonds
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A highly efficient method for the synthesis of S-aryl dithiocarbamates is reported. By using tetramethylthiuram monosulfide (TMTM) and aryl boronic acids as starting materials, C(sp2)-S bondforming reactions proceed smoothly to give the desired aryl dithiocarbamates in good to excellent yields. The methodology features a simple procedure, broad functional group tolerance and excellent yields, whilst showing potential synthetic value for the preparation of a diverse range of biologically and pharmaceutically active compounds.
- Xia, Xu-Ling,Zhu, Qi-Long,Chen, Jin-Quan,Shi, Zhen,Dong, Zhi-Bing
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supporting information
p. 475 - 482
(2021/10/25)
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- An Efficient Copper-Catalyzed C(sp 2)-S Formation Starting from Aryl Iodides and Tetramethylthiuram Monosulfide (TMTM)
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A new, efficient copper-catalyzed C(sp 2)-S formation of phenyl dithiocarbamates starting from aryl iodides and tetramethylthiuram monosulfide (TMTM) was developed. The target compounds, phenyl dithiocarbamates with active sites, were synthesized smoothly in good to excellent yields. The easy performance, high yields, decent functional group compatibility, and cost-effective substrates make the protocol practical and attractive in C-S bond formation.
- Wu, Yue-Xiao,Peng, Kang,Li, Jing-Hang,Dong, Zhi-Bing
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supporting information
p. 3001 - 3006
(2020/08/12)
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- Chemoselective C–S/S–S Formation between Diaryl Disulfides and Tetraalkylthiuram Disulfides
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An efficient C–S/S–S formation for the chemoselective synthesis of aryl dithiocarbamate (C–S formation) and aryl dialkylcarbamo(dithioperoxo)thioate (S–S formation) was studied. The chemoselectivity could be controlled by modulating the reaction temperature, base, and catalyst. The transformation features a simple reaction, easily available starting materials, high selectivity and easy performance, showing its practical synthetic value for the preparation of some potential biologically or pharmaceutically active compounds.
- Peng, Kang,Zhu, Hui,Liu, Xing,Peng, Han-Ying,Chen, Jin-Quan,Dong, Zhi-Bing
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p. 7629 - 7634
(2019/12/03)
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- Copper-Catalyzed Synthesis of S-Aryl Dithiocarbamates from Tetraalkylthiuram Disulfides and Aryl Iodides in Water
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An efficient approach for the copper-catalyzed synthesis of aryl dithiocarbamates from aryl iodides and tetraalkylthiuram disulfides in water is described. Without additional ligand and organic solvent, the coupling reaction could provide a series of S-aryl dithiocarbamates in moderate to good yields.
- Wu, Xiang-Mei,Yan, Guo-Bing
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supporting information
p. 610 - 614
(2019/03/08)
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- Synthesis of Phenyl Dithiocarbamates Starting from Sodium Dialkyldithiocarbamates and Aryl Boronic Acids: a Copper Catalyzed S-Arylation
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A convenient and efficient protocol for the S-arylation of sodium dialkyldithiocarbamates was developed. With the catalysis of copper(I) bromide, sodium dialkyldithiocarbamates coupled with aryl boronic acids giving the C-S coupling products smoothly in g
- Gao, Ming-Yuan,Xu, Wan,Zhang, Shi-Bo,Li, Yue-Sheng,Dong, Zhi-Bing
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p. 6693 - 6698
(2018/11/25)
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- Copper-Catalyzed S-Arylation Starting from Arylboronic Acids and Tetraalkylthiuram Disulfide
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A convenient and useful protocol for the synthesis of diverse S-aryl dithiocarbamates was studied. Starting from arylboronic acid and tetraalkylthiuram disulfide, copper-catalyzed C–S coupling proceeds smoothly to give the desired S-aryl dithiocarbamates in good to excellent yields. The broad substrate scope, short reaction time, easy performance, cheap substrates, and nice yields make this approach attractive, showing its practical synthetic value for the preparation of some biologically or pharmaceutically active compounds.
- Xu, Wan,Gao, Fan,Dong, Zhi-Bing
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p. 821 - 828
(2018/02/21)
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- A Highly Efficient CuCl 2 -Catalyzed C-S Coupling of Aryl Iodides with Tetraalkylthiuram Disulfides: Synthesis of Aryl Dithiocarbamates
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A highly efficient copper(II)-catalyzed C-S cross-coupling reaction of aryl iodides with tetraalkylthiuram disulfides was developed. With only 1 mol% of CuCl 2 as catalyst, zinc powder as reductant, and K 2 CO 3 as base, aryl iodides reacted with tetraalkylthiuram disulfides in DMSO furnishing the corresponding aryl dithiocarbamates in good to excellent yields. This protocol is an improvement of previous work, it features convenient performance, low addition of catalyst, no requirement for any ligand, and provides good yields. The method has a broad substrate scope and uses cheap and readily available starting materials.
- Cao, Qiang,Peng, Han-Ying,Cheng, Yu,Dong, Zhi-Bing
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p. 1527 - 1534
(2018/01/17)
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- Copper-Catalyzed C(sp2)-S Coupling Reactions for the Synthesis of Aryl Dithiocarbamates with Thiuram Disulfide Reagents
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An efficient protocol for the copper-catalyzed preparation of aryl dithiocarbamates from aryl iodides and inexpensive, environmentally benign tetraalkylthiuram disulfides was developed. The features of mild reaction conditions, high yields, and broad substrate scope render this new approach synthetically attractive for the preparation of potentially biologically active compounds.
- Dong, Zhi-Bing,Liu, Xing,Bolm, Carsten
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supporting information
p. 5916 - 5919
(2017/11/10)
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- Transition-Metal-Free C-S Bond Formation: Aqueous Synthesis of S-Aryl Dithiocarbamates by the use of Stable Arenediazonium Salts Mediated by Nano-Magnetic Supported Silica Sulfonic Acid
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A convenient and transition-metal-free method for the synthesis of S-aryl dithiocarbamates based on the reaction of stable arenediazonium nano-magneto silica sulfates (ArN2+-OSO3-SiO2@Fe3O4) with dithiocarbamic acid at room temperature was studied. Avoiding the use of any hazardous transition metal, simple procedure, low cast, and short reaction time are noteworthy advantages of this methodology.
- Nemati, Firouzeh,Elhampour, Ali,Zulfaghari, Soghra
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p. 1692 - 1702
(2015/09/15)
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- Transition metal-free procedure for the synthesis of S-aryl dithiocarbamates using aryl diazonium fluoroborate in water at room temperature
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A convenient, efficient and green procedure for the synthesis of S-aryl dithiocarbamates has been developed by a simple one-pot condensation of aryl diazonium fluoroborate, carbon disulfide and amine in the absence of any transition metal catalyst in water at room temperature. The reactions of a variety of substituted aryl diazonium fluoroborates, and cyclic and open chain amines, have been addressed. The products are purified by crystallization from ethanol and the process does not involve any hazardous solvent.
- Chatterjee, Tanmay,Bhadra, Sukalyan,Ranu, Brindaban C.
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experimental part
p. 1837 - 1842
(2011/10/01)
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- A new method for the synthesis of dithiocarbamates by CuI-catalyzed coupling reaction
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The Ullmann-type coupling reaction of sodium dithiocarbamates with aryl iodides and vinyl bromides catalyzed by CuI/N,N-dimethylglycine proceeds smoothly in DMF at 110 °C to give corresponding dithiocarbamates in good yields.
- Liu, Yunyun,Bao, Weiliang
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p. 4785 - 4788
(2008/02/07)
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- Synthesis of dithiocarbamates and selenothiocarbamates
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Several dithiocarbamates and selenothiocarbamates were synthesized by the reaction of N,N-dimethylthiocarbamoyl chloride with the corresponding thiolates and selenolates.
- Koketsu, Mamoru,Otsuka, Toshihiro,Ishihara, Hideharu
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p. 443 - 448
(2007/10/03)
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- Hypervalent iodine in synthesis 58: Synthesis of aryl esters of dithiocarbamic acids using polymeric diaryliodonium salts
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Polymer-supported diaryliodonium salts were prepared and employed as aryl transfer reagents for the synthesis of aryl esters of dithiocarbamic acids.
- Chen,Chen
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p. 352 - 353
(2007/10/03)
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- Cycloaddition in synthesis of sulfonamide derivatives. IV. One-pot synthesis of 3-dimethylamino-4,1,2-benzoxathiazine 1,1-dioxides, 3-methoxy-4-methyl-1,2,4-benzothiadiazine 1,1-dioxide and 3-dimethylamino-1,4,2-benzodithiazine 1,1-dioxides
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A novel, one-pot synthesis of 3-dimethylamino-4,1,2-benzoxathiazine 1,1-dioxides (7), 3-methoxy-4-methyl-1,2,4-benzothiadiazine 1,1-dioxide (9) and 3-dimethylamino-1,4,2-benzodithiazine 1,1-dioxides (11) is described. The procedure in the case of 7 involv
- Iwakawa,Tamura,Murabayashi,Hayase
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p. 1939 - 1943
(2007/10/02)
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