Electrochemical Sulfonylation of Alkynes with Sulfonyl Hydrazides: A Metal- and Oxidant-Free Protocol for the Synthesis of Alkynyl Sulfones
Herein, an electrochemical oxidative cross-coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and transition metal- and oxidant-free conditions. Most of the compounds exhibit good inhibitory activity on tumor cell lines, and one of the compounds can inhibit cell migration and induce apoptosis in HeLa cells. (Figure presented.).
The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers
tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.
Zhang, Wenhan,Ready, Joseph M.
supporting information
p. 8980 - 8984
(2014/11/07)
Synthesis of alkyl-ynol-ethers by anti-Michael addition of metal alkoxides to β-substituted alkynylsulfones
The reaction of metal alkoxides with β-substituted 2-(p-tolylsulfonyl)acetylenes, involving an anti-Michael addition reaction followed by the in situ elimination of the sulfonyl moiety, provides a direct method for the synthesis of alkyl alkynyl ethers bearing aryl or TIPS groups joined to the triple bond. Arylalkynyl ethers derived from primary alkoxides are in situ hydrolyzed into arylacetic esters. Copyright
Marzo, Leyre,Parra, Alejandro,Frias, Maria,Aleman, Jose,Garcia Ruano, Jose Luis
p. 4405 - 4409
(2013/07/26)
Transition-metal-free synthesis of aryl-substituted tert-butyl ynol ethers through addition/elimination substitution at an sp centre
Nucleophilic attack of an alkoxide on an alkynyl sulfonamide leads to displacement of the sulfonamide at the sp centre and isolation of the ynol ether in good yield in a single operation (see scheme). The mechanistic pathway has been probed by the use of coordinating additives, 13C-labelling experiments and ab initio calculations, which indicated that an addition/elimination mechanism is in operation. Copyright
Gray, Vincent J.,Slater, Ben,Wilden, Jonathan D.
p. 15582 - 15585
(2013/01/16)
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