73542-36-6Relevant articles and documents
Additive-Controlled Switchable Selectivity from Cyanobenzenes to 2-Alkynylpyridines: Ruthenium(II)-Catalyzed [2+2+2] Cycloadditions of Diynes and Alkynylnitriles
Bhatt, Divya,Patel, Neha,Chowdhury, Hrishikesh,Bharatam, Prasad V.,Goswami, Avijit
supporting information, p. 1876 - 1882 (2018/04/11)
A highly efficient additive-dependent chemoselective protocol for the synthesis of fused cyanoarenes and 2-alkynylpyridines has been developed by the reaction of 1,6-diynes with alkynylnitriles using chloro(pentamethylcyclopentadienyl) (cyclooctadiyne)ruthenium(II) as catalyst in dimethoxyethane (DME). The course of the reaction can be drastically altered simply by adding a catalytic amount of AgOTf as an additive resulting in a comprehensive shift in product formation from cyanoarenes to 2-alkynylpyridines. Theoretical studies clearly indicate that the neutral Ru-complex is responsible for the formation of cyanobenzenes, whereas the in situ generated cationic Ru-complex plays a crucial role in the 2-alkynylpyridines formation. (Figure presented.).
Stereoselective silylcupration of conjugated alkynes in water at room temperature
Linstadt, Roscoe T. H.,Peterson, Carl A.,Lippincott, Daniel J.,Jette, Carina I.,Lipshutz, Bruce H.
, p. 4159 - 4163 (2014/05/06)
Micellar catalysis enables copper-catalyzed silylcupration of a variety of electron-deficient alkynes, thereby providing access to isomerically pure E- or Z-β-silyl-substituted carbonyl derivatives. These reactions take place in minutes, afford high yields and stereoselectivity, and are especially tolerant of functional groups present in the substrates. The aqueous reaction medium has been successfully recycled several times, and a substrate/catalyst ratio of 10,000:1 has been documented for this methodology. Fast, cheap, and green: Micellar catalysis enables the selective construction of a variety β-silyl-substituted carbonyl derivatives under mild aqueous conditions. The reaction is catalyzed by low levels of CuI, is compatible with numerous electron-withdrawing groups, affords high yields, and provides opportunities for scale-up and recycling of the reaction medium. The environmental impact, as measured by E Factors, is very low.
Synthesis and Identification of Solution-Stable Sulfenic Acids: Perfluoroalkanesulfenic Acids
Li, Xiao-Bo,Xu, Ze-Feng,Liu, Li-Juan,Liu, Jin-Tao
supporting information, p. 1182 - 1188 (2015/10/05)
Taking advantage of the strong electron-withdrawing effect of perfluoroalkyl groups, solution-stable perfluoroalkanesulfenic acids were synthesized for the first time by Cope-type elimination of the corresponding imines; the acids were identified by 1H NMR, 19F NMR, and IR spectroscopy and mass spectrometry. Trapping reagents were utilized to capture the in situ generated sulfenic acids, which provided further experimental evidence for the formation of these fluorinated sulfenic acids.
