57440-42-3Relevant articles and documents
Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids
Senaweera, Sameera,Cartwright, Kaitie C.,Tunge, Jon A.
, p. 12553 - 12561 (2019/10/14)
Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C-O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An alternative approach is to use ubiquitous carboxylic acids as starting materials and perform a decarboxylative coupling. Herein, we report conditions for a photocatalytic decarboxylative C-O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products. Mechanistic investigations suggest that the reaction operates via oxidation of the carboxylate followed by rapid decarboxylation and oxidation by Cu(OAc)2
Electrochemical Properties and Reactions of Sulfur-Containing Organoboron Compounds
Tanigawa, Masahiro,Kuriyama, Yu,Inagi, Shinsuke,Fuchigami, Toshio
, p. 314 - 318 (2016/04/26)
Electrochemical analyses of 4,4,5,5-tetramethyl-2-phenylsulfanylmethyl-[1,3,2]dioxaborolane and tetra-n-butylammonium phenylthiomethyltrifluoroborate were comparatively studied by cyclic voltammetry measurements and we found for the first time the β-effect of organoborate, which was indicated by experimental and theoretical aspects. The organoborate was found to have a much lower oxidation potential compared to the organoborane. Anodic substitution reaction of organoboronate ester and organoborate was successfully carried out in the presence of nucleophiles to afford the selectively substituted products in good yields.
Direct α-acyloxylation of organic sulfides with the hypervalent (diacyloxyiodo)benzene/tetra-n-butylammonium bromide (TBAB) reagent combination
Zhu, Dan,Chang, Denghu,Gan, Shaoyan,Shi, Lei
, p. 27983 - 27987 (2016/04/04)
A novel metal-free approach to directly synthesize α-acyloxy sulfides from readily available alkyl sulfides utilizing the hypervalent (diacyloxyiodo)benzene and TBAB reagent combination is reported. This transformation is characterized by its broad substrate scope in moderate to excellent yields, convenient operating conditions and outstanding functional group tolerance.