- Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols
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Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of a copper(ii) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluoroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones in up to 94% yields. The experimental protocol is mild and tolerates a number of functionalities in the cyclopropanol substrate. The reaction proceeds via a one-pot oxidation-Michael addition mechanism and can serve as a useful addition to the existing methods for the preparation of γ-keto sulfones based on the sulfa-Michael reaction.
- Konik, Yulia A.,Elek, Gábor Zoltán,Kaabel, Sandra,J?rving, Ivar,Lopp, Margus,Kananovich, Dzmitry G.
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- SYNTHESIS OF CARBONYL COMPOUNDS USING ORGANOMANGANESE PENTACARBONYL COMPLEXES.
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Sequential insertion of carbon monoxide and either strained or electron deficient alkenes into alkylmanganese pentacarbonyl complexes at pressures of 6 kbar provides manganacycles in a regioselective and stereoselective fashion.The manganacycles can be transformed into carbonyl compounds under photolytic conditions.
- DeShong, Philip,Slough, Greg A.,Rheingold, Arnold L.
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- Regioselective Arene and Heteroarene Functionalization: N-Alkenoxypyridinium Salts as Electrophilic Alkylating Agents for the Synthesis of α-Aryl/α-Heteroaryl Ketones
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A direct regioselective functionalization of arenes and heteroarenes using N-alkenoxypyridinium salts as electrophilic alkylating agents for the synthesis of α-aryl/heteroaryl ketones has been developed. The method generates alkylating agents from alkynes and N-pyridine oxide followed by site-selective electrophilic substitution with a broad range of arenes and heteroarenes including benzene derivates, phenols, ethers, indoles, pyrroles, furans, and thiophenes in one pot. Kinetic isotope effect measurements and DFT studies reveal that this reaction likely proceeds through a carbon-cation intermediate.
- Zhai, Rong L.,Xue, Yun S.,Liang, Ting,Mi, Jia J.,Xu, Zhou
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p. 10051 - 10059
(2018/07/30)
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- Efficient synthesis of γ-keto sulfones by NHC-catalyzed intermolecular Stetter reaction
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The N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aldehydes with α,β-unsaturated sulfones allows the atom-economic and selective formation of γ-keto sulfones in good yields. Key to the success of this unique transition-metal-free carbon-carbon bond-forming reaction is the right choice of the NHC precursor and base. The reaction tolerates a broad range of different aldehydes.
- Bhunia, Anup,Yetra, Santhivardhana Reddy,Bhojgude, Sachin Suresh,Biju, Akkattu T.
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supporting information; experimental part
p. 2830 - 2833
(2012/07/17)
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