175658-16-9Relevant articles and documents
Electroorganic synthesis using a fluoride ion mediator under ultrasonic irradiation: Synthesis of oxindole and 3-oxotetrahydroisoquinoline derivatives
Shen, Yi,Atobe, Mahito,Fuchigami, Toshio
, p. 2441 - 2444 (2004)
(Equation Presented) Anodic intramolecular cyclization of α-(phenylthio)acetamides using a fluoride ion mediator was realized. Under ultrasonic irradiation, cyclization was accelerated markedly to give desired cyclized products in moderate to good yields.
Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities
Kondoh, Azusa,Oishi, Masafumi,Terada, Masahiro,Tezuka, Hikaru
supporting information, p. 7472 - 7477 (2020/03/19)
In the field of chiral Br?nsted base catalysis, a new generation of chiral catalysts has been highly anticipated to overcome the intrinsic limitation of pronucleophiles that are applicable to the enantioselective reactions. Herein, we reveal conceptually new chiral Br?nsted base catalysts consisting of two different organobase functionalities, one of which functions as an organosuperbase and the other as the substrate recognition site. Their prominent activity, which stems from the distinctive cooperative function by the two organobases in a single catalyst molecule, was demonstrated in the unprecedented enantioselective direct Mannich-type reaction of α-phenylthioacetate as a less acidic pronucleophile. The present achievement would provide a new guiding principle for the design and development of chiral Br?nsted base catalysts and significantly broaden the utility of Br?nsted base catalysis in asymmetric organic synthesis.
Fluorination of sulfanyl amides using difluoroiodoarene reagents
Motherwell, William B.,Greaney, Michael F.,Edmunds, Jeremy J.,Steed, Jonathan W.
, p. 2816 - 2826 (2007/10/03)
A range of sulfur-containing amides have been fluorinated with the hypervalent iodine difluoride reagents 1, and two principal reaction pathways identified. Cephalosporin esters 2 having a heteroatom in the α-position to sulfur undergo fluorination in DCM with cleavage of the carbon-sulfur bond to form novel fluorinated β-lactams 4. Sulfides with electron-withdrawing groups in the α-position undergo α-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple α-phenylsulfanylacetamides 14-19. When β-hydrogens are present in the substrate a different route is followed, with deprotonation by basic fluoride taking place to yield vinyl sulfides 41-43. When an excess of the fluorinating reagent is used these vinyl sulfides can undergo further reaction in a novel tandem Pummerer-Additive-Pummerer process to yield α,β-difluoro sulfides 45-47.
