59555-69-0Relevant academic research and scientific papers
Base-Mediated Radical Borylation of Alkyl Sulfones
Huang, Mingming,Hu, Jiefeng,Krummenacher, Ivo,Friedrich, Alexandra,Braunschweig, Holger,Westcott, Stephen A.,Radius, Udo,Marder, Todd B.
supporting information, (2021/12/02)
A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.
SYNTHESES WITH SULFONES XLVIII : STEREOSELECTIVE SYNTHESIS OF 2-ISOPROPYL 1,4-DIENES THROUGH THE IRON-CATALYSED CROSS-COUPLING REACTION OF 2-BENZENESUFONYL 1,4-DIENES AND ISOPROPYLMAGNESIUM CHLORIDE.
Alvarez, E.,Cuvigny, T.,Penhoat, Herve C. du,Julia, M.
, p. 111 - 118 (2007/10/02)
The stereoselective sythesis of 2-isopropyl 1,4-dienes and isopropylmagnesium chloride under transition-metal catalysis is described.Iron salts, which were better catalysis than palladium or nickel ones, led to substitution of the sulfonyl group with >97percent stereospecificity and without isomerization of the isopropyl Grignard moiety to the n-propyl derivative.Notable amounts of the compound resulting from reduction of the sulfonyl group were also formed.
IODINE-INDUCED IMINOTHIOLACTONIZATION OF γ,δ-UNSATURATED SECONDARY THIOAMIDES, NEW ENTRY TO 2-ACETOAMIDOTHIOPHENES
Takahata, Hiroki,Suzuki, Toshiaki,Maruyama, Mihoko,Moriyama, Keiko,Mozumi, Mayumi,et.al.
, p. 4777 - 4786 (2007/10/02)
Iodine-induced cyclization of γ,δ-unsaturated secondary thioamides 1 proceeded regio- (5-exo-trigonal) and chemo- (sulfur-carbon bond formation)selectively, providing iminothiolactones 2, which were converted in two-step sequences (dehydroiodination and N-acetylation) into 2-acetoamidothiophenes 4.This procedure was performed in one flask to afford polysubstituted 2-aminothiophenes.
