- Cross-coupling reaction of organoalane reagents with 2-mercaptobenzo-5-membered heterocycles for efficient synthesis of benzo-5-membered heterocycle sulfides
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A highly efficient and simple route for the synthesis of benzo-5-membered heterocycles sulfides has been developed by the cross-coupling reaction of 2-mercaptobenzo-5-membered heterocycles with (hetero)arylaluminum reagents. Various benzo-5-membered heter
- Luo, Rui-Qiang,Guo, Shao Peng,Xiao, Hong-Liu,Li, Qing-Han
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- Visible-Light-Mediated Synthesis of Unsymmetrical Diaryl Sulfides via Oxidative Coupling of Arylhydrazine with Thiol
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A metal-free visible-light-promoted oxidative coupling between thiols and arylhydrazines has been developed to afford diaryl sulfides using a catalytic amount of rose bengal as photocatalyst under aerobic conditions. A library of unsymmetrical diaryl sulfides with broad functionalities was synthesized in good yields at room temperature. The present methodology is also applicable to benzo[d]thiazole-2-thiols, benzo[d]oxazole-2-thiol, 1H-benzo[d]imidazole-2-thiols, and 1H-imidazole-2-thiol.
- Kibriya, Golam,Mondal, Susmita,Hajra, Alakananda
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supporting information
p. 7740 - 7743
(2018/12/14)
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- N-heterocyclic carbene copper(I) complex-catalyzed direct C-H thiolation of benzothiazoles
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N-heterocyclic carbene (NHC) copper(I) complexes based on imidazol-2-ylidene and 1,2,3-triazol-5-ylidene catalyzed the direct C-H thiolation of benzothiazoles and benzoxazoles with aryl and alkyl thiols to give 2-aryl and 2-alkylthiobenzothiazoles in moderate-to-good yields. The NHC copper(I) complex [(IPr)CuI] was the most effective catalyst for the reaction among the NHC-Cu(I) complexes examined in this study.
- Inomata, Hiroshi,Toh, Ayumi,Mitsui, Takashi,Fukuzawa, Shin-Ichi
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supporting information
p. 4729 - 4731
(2013/08/23)
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- Copper oxide nanoparticle-catalyzed chalcogenation of the carbon-hydrogen bond in thiazoles: Synthesis of 2-(organochalcogen) thiazoles
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We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/dio-rganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydro-gen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromat-ic ring bonded to the chalcogen atom of diorganyl di-chalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.
- Rosario, Alisson R.,Casola, Kamila K.,Oliveira, Carla E.S.,Zeni, Gilson
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supporting information
p. 2960 - 2966
(2014/03/21)
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- Substrate-promoted ligand-free CuI catalyzed S-arylation of 2-mercaptobenzothiazoles with aryl iodides in water
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A green and efficient method has been developed for the cross-coupling of 2-mercaptobenzothiazoles with aryl iodides in water. The reactions proceeded smoothly under ligand-free conditions in the presence of TBAB to give the corresponding products in good yields. The protocol showed good tolerance toward a variety of functional groups. A substrate-promoted mechanism for this catalytic reaction has been proposed.
- He, Guozhen,Huang, Yuan,Tong, Yao,Zhang, Jie,Zhao, Dan,Zhou, Shuangli,Han, Shiqing
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supporting information
p. 5318 - 5321
(2013/09/12)
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- Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio)isobutyrophenone
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In the presence of catalytic amounts of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with α-(phenylthio) isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds.
- Arisawa, Mieko,Toriyama, Fumihiko,Yamaguchi, Masahiko
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supporting information; experimental part
p. 2344 - 2347
(2011/05/16)
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- Copper(I)-catalyzed cascade synthesis of 2-substituted 1,3-benzothiazoles: Direct access to benzothiazolones
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An efficient cascade process for the preparation of 2-substituted 1,3-benzothiazoles directly from 2-haloaryl isothiocyanates and O or S nucleophiles by a Cu-catalyzed, intramolecular, C-S bond formation has been developed. This cascade method is viable f
- Murru, Siva,Mondal, Pravat,Yella, Ramesh,Patel, Bhisma K.
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experimental part
p. 5406 - 5413
(2010/02/28)
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- Intra- and Intermodular C-S bond formation using a single catalytic system: First direct access to arylthiobenzothiazoles
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We have for the first time developed two llgand-assisted Cu(I)-catalyzed sequential Intra- and intermolecular 5-arylations leading to the direct synthesis of arylthiobenzothlazoles In one pot without an Inert atmosphere. Low catalyst loading, inexpensive
- Murru, Siva,Ghosh, Harisadhan,Sahoo, Santosh K.,Patel, Bhisma K.
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supporting information; experimental part
p. 4254 - 4257
(2010/01/06)
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