66693-07-0Relevant academic research and scientific papers
FLP-catalysis meets hydrogen-bond activation
K?ring, Laura,Paradies, Jan,Roesky, Peter W.,Sitte, Nikolai A.
, p. 7321 - 7325 (2020/10/13)
The potential of two chiral amidines and three non-chiral boranes in the metal-free hydrogen activation was explored. The resulting chiral amidiunium borohydride salts were investigated in asymmetric hydrogenation reactions of ketimines, activated double bonds and dehydro amioacid esters.
Tuning the lewis acidity of boranes in frustrated lewis pair chemistry: Implications for the hydrogenation of electron-poor alkenes
Nicasio, Juan A.,Steinberg, Sebastian,Ines, Blanca,Alcarazo, Manuel
, p. 11016 - 11020 (2013/09/02)
An analysis of the metal-free reduction of electron deficient olefins by frustrated Lewis pairs indicates that the rate-determining step might be either the heterolytic cleavage of H2 to form an -onium borohydride salt, or the subsequent transfer of the hydride moiety to the substrate following a Michael-type addition reaction. While the use of strong Lewis acids such as B(C6F5)3 facilitates the first of these processes, hydride transfer to the olefin should be contrarily favoured by the use of weak Lewis acids which, for this very same reason, might be unable to promote the prior H2 split. After systematic testing of several boranes of different Lewis acidity (assessed by using the Childs' method) and steric demand, an optimal situation that employs tris(2,4,6-trifluorophenyl) borane was reached. Mixtures of this borane with 1,4-diazabicyclo[2.2.2]octane (DABCO) exhibited excellent catalytic activity for the hydrogenation of alkylidene malonates. In fact, this transformation could be achieved under milder conditions than those we reported previously. Moreover, the reaction scope could be expanded to other electron deficient olefins containing esters, sulfones or nitro functionalities as electron-withdrawing substituents.
Solid-liquid phase transfer catalytic synthesis V III: The rapid alkylation of ethyl phenylsulfonylacetate under microwave irradiation
Wang,Jiang
, p. 2287 - 2291 (2007/10/02)
Rapid alkylations of ethyl phenylsufonylacetate with a series of halides were performed in 960 W domestic microwave oven, and the isolated yield of α-monoalkylated product varying from 76 to 86%.
A CONVENIENT SYNTHESIS OF PHENYLSULFONYLALKANOIC ACIDS
Ratajczak, Aleksander,Polanski, Jaroslaw
, p. 1271 - 1275 (2007/10/02)
Ethyl phenylsulfonylacetate is alkylated in high yields with alkyl halides in toluene/K2CO3 two-phase system with TEBA (TBAB) as a catalyst.
Chemistry of Novel Compounds with Multifunctional Carbon Structure. 5. Molecular Design of Versatile Building Blocks for Aliphatic Monofluoro Molecules by Manipulation of Multifunctional Carbon Structure
Takeuchi, Yoshio,Nagata, Kazuhiro,Koizumi, Toru
, p. 5453 - 5459 (2007/10/02)
Three kinds of doubly functionalized monofluoromethylene fragments, 1-fluoro-1-nitro-1-(phenylsulfonyl)alkanes (10), 2-fluoro-2-(phenylsulfonyl)alkanoic esters (11), and 2-fluoro-2-nitroalkanoic esters (12), potentially versatile building blocks for the general synthesis of various aliphatic monofluoro molecules, were prepared from the corresponding difunctional compounds 1-3 by monoalkylation (R) and selective fluorinations.The interconversion or reductive removal of each functional group in 10-12 followed by the introduction of the second alkyl groups (R') at the fluorine-bearing carbon atom was examined.Compounds 12 proved to be useful and practical building blocks for conversions to the various monofluoroalkanes 20-26.
