1754-62-7Relevant articles and documents
Photodimerization of hydrophobic guests within a water-soluble nanocapsule
Parthasarathy, Anand,Samanta, Shampa R.,Ramamurthy
, p. 73 - 87 (2013)
Conducting reactions in environmentally benign conditions is one of the major objectives of "green chemistry." In this context, developing ways to conduct reactions in water seems obvious. In this report, we present our results on photodimerization of sel
Corey,Hegedus
, p. 1233 (1969)
A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still-Gennari Type Phosphonates
Janicki, Ignacy,Kie?basiński, Piotr
, p. 378 - 382 (2021/10/21)
Z-Selective Still-Gennari and Ando modifications of the typically E-selective Horner-Wadsworth-Emmons reaction are highly valuable synthetic tools in organic chemistry. These procedures are based on application of bis(2,2,2-trifluoroethyl) phosphonates or diaryl phosphonates, respectively, for the olefination of carbonyl groups. In our research, we present an improved, straightforward, purificationfree procedure for the synthesis of these reagents. The key step of our procedure is the reaction of phosphonic dichlorides with the appropriate sodium alkoxides, which results in 52-97% isolated yields of the desired products on a gram scale. The whole three-step process is performed in one pot. Most importantly, the product is obtained in over 95% purity after simple extraction, avoiding column chromatography and distillation. Moreover, we present the synthesis of a novel Still-Gennari type reagent, bis(1,1,1,3,3,3-hexafluoroisopropyl) phosphonates, which may exhibit improved Z-selectivity in Still-Gennari olefinations.
Visible-Light-Driven Isocyanide Insertion to o-Alkenylanilines: A Route to Isoindolinone Synthesis
Dahiya, Anjali,Das, Bubul,Sahoo, Ashish Kumar,Patel, Bhisma K.
, p. 966 - 973 (2022/02/07)
A visible-light-mediated intermolecular radical insertion of isocyanides to electron-deficient o-alkenylanilines leading to isoindolinone is reported. Deuterium (D2O) and H2O18 labelling experiments suggest H and O incorporation in the product. The formation of an N-centered radical (NCR) via stepwise PT/ET process was confirmed by radical trapping experiments, photoluminescence, cyclic voltammetry and DFT studies. This photo cascade methodology is overall a redox neutral process featuring metal-free condition and broad substrate scope (32 examples). The synthesis of analogue of GABA receptor antagonist shows the practical utility of this method. (Figure presented.).
Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
Valiente, Alejandro,Martínez-Pardo, Pablo,Kaur, Gurpreet,Johansson, Magnus J.,Martín-Matute, Belén
, (2021/12/22)
Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes was developed, using a simple nickel foam as catalyst and H3O+ or D3O+ as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.