- Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides
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The cross-electrophile coupling between unactivated alkyl bromides with arenesulfonyl cyanides catalyzed by Ni(acac)2under reductive conditions to form unsymmetrical sulfides is developed. This approach for sulfide synthesis is practical, relies on available, unfunctionalized materials such as alkyl (pseudo)halides, and is scalable. This catalytic strategy provides a complementary method for the preparation of unsymmetrical alkyl-aryl sulfides under mild conditions with good functional group tolerance.
- Rao, Weidong,Wang, Fei,Wang, Shun-Yi
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p. 8970 - 8979
(2021/07/19)
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- Solvent-free synthesis of arylsulfonyl cyanides using potassium hexacyanoferrate(II) as an ecofriendly cyanide source
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A solvent-free synthetic method for arylsulfonyl cyanides directly from corresponding sulfonyl chlorides using potassium hexacyanoferrate(II) as an ecofriendly cyanide source is described. The protocol has the advantages of no uses of highly toxic cyanating agent and volatile organic solvents, high yield, and simple work-up procedures.
- Li, Zheng,Xu, Jun
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p. 374 - 378
(2014/03/21)
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- Process for producing 2-azabicyclo[2.2.1]hept-5-en-3-one
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2-Azabicyclo[2.2.1]hept-5-en-3-one is prepared by a process comprising: continuously mixing a substituted sulfonyl cyanide represented by formula (I): R—SO2CN??(I), wherein R represents an alkyl group or a phenyl group or a substituted phenyl group, with cyclopentadiene; and then continuously adding the resultant reaction solution to water or to a mixed solvent comprising water and a hydrocarbon solvent under the condition that the pH of the present reaction mixture ranges from 4 to 7.
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- Process for producing and method of crystallizing 2-azabicyclo[2.2.1]hept-5-en-3-one
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A process for producing 2-azabicyclo[2.2.1]hept-5-en-3-one is provided by reacting a sulfonyl cyanide represented by the general formula R-SO2CN (in which R represents an alkyl group or a phenyl group which may have a substituent), in the presence of water and in a hydrocarbon solvent at a pH of 4 to 7 inclusive. 2-Azabicyclo[2.2.1]hept-5-en-3-one can be produced in a high yield and a high purity in one step process, with a reduced amount of solvent used, safely and with good productivity. A method of crystallizing 2-azabicyclo[2.2.1]hept-5-en-3-one is also provided, which includes dissolving 2-azabicyclo[2.2.1]hept-5-en-3-one into an organic solvent mainly including at least one of diisopropyl ether and methyl tertiary butyl ether, cooling the solution to deposit crystals of 2-azabicyclo[2.2.1]hept-5-en-3-one. Finely divided particulate crystals of 2-azabicyclo[2.2.1]hept-5-en-3-one excellent in fluidity and handleability can be obtained with a simple procedure and in a high recovery rate.
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