129112-25-0Relevant articles and documents
Pd(II)-catalyzed P(O)R1R2-directed asymmetric C-H activation and dynamic kinetic resolution for the synthesis of chiral biaryl phosphates
Ma, Yan-Na,Zhang, Hong-Yu,Yang, Shang-Dong
, p. 2034 - 2037 (2015)
An efficient method of Pd(II)-catalyzed P(O)R1R2-directed asymmetric C-H activation and dynamic kinetic resolution for synthesis of chiral phosphinate ligands has been performed and exhibits a wide scope of substrates and an excellen
SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates
Alonso, Mercedes,De Borggraeve, Wim M.,Demaerel, Joachim,Hoppenbrouwers, Fien,Li, Bing-Yu,Van Lommel, Ruben,Verhelst, Steven H. L.,Voets, Lauren
, p. 2270 - 2279 (2022/03/08)
Sulfur(vi) Fluoride Exchange (SuFEx) chemistry has emerged as a next-generation click reaction, designed to assemble functional molecules quickly and modularly. Here, we report the ex situ generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use as a new SuFEx handle to efficiently synthesize triflates and triflamides. This broadly tolerated protocol lends itself to peptide modification or to telescoping into coupling reactions. Moreover, redesigning the SVI-F connector with a SO → SNR replacement furnished the analogous triflimidoyl fluorides as SuFEx electrophiles, which were engaged in the synthesis of rarely reported triflimidate esters. Notably, experiments showed H2O to be the key towards achieving chemoselective trifluoromethanesulfonation of phenols vs. amine groups, a phenomenon best explained - using ab initio metadynamics simulations - by a hydrogen bonded termolecular transition state for the CF3SO2F triflylation of amines. This journal is
Rapid Room-Temperature, Chemoselective Csp2?Csp2Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air
Kalvet, Indrek,Magnin, Guillaume,Schoenebeck, Franziska
supporting information, p. 1581 - 1585 (2017/02/05)
While chemoselectivities in Pd0-catalyzed coupling reactions are frequently non-intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on PdIthat allows for an a priori predictable chemoselective Csp2?C Csp2coupling at C?Br in preference to C?OTf and C?Cl bonds, regardless of the electronic or steric bias of the substrate. The C?C bond formations are extremely rapid (Idimer under open-flask conditions.