The first regioselective phenoxysulfonylation of alkynes with sodium sulfinate and phenol catalyzed by I 2 /base has been uncovered. This metal-free, one-pot alkyne difunctionalization process provides various (Z)-β-phenoxy vinylsulfones under mild reaction conditions. A variety of terminal as well as internal alkynes and sodium sulfinates and a wide range of phenols/thiophenols and naphthols are viable in this transformation. Green protocol and wide substrate scope are the remarkable characteristics of this multicomponent procedure.
An efficient amino acid-catalyzed
protocol for the synthesis of
β-keto sulfones using terminal alkynes and arylsulfinic acid
sodium salts under aerobic conditions in water/AcOH has been developed.
This reaction involves an in situ generated vinyl radical intermediate
and an atom transfer radical addition (ATRA) process via oxygen capture
to form the desired products in good to excellent yields. This protocol
is operationally simple and environmentally friendly and proceeds
under very mild conditions.
A copper-catalyzed decarboxylative regioselective protocol for the synthesis of 1,5-disubstituted 1,2,3-triazoles through direct annulation of cinnamic acids with aryl azides has been developed. This is the first example of 1,5-disubstituted 1,2,3-triazoles, under aerobic conditions using Cu(ii) as the catalyst, which were generally synthesized using a ruthenium(ii) catalyst. The simplicity and regioselectivity of this methodology, complementing to the classical CuAAC catalyzed the synthesis of 1,4-disubstituted 1,2,3-triazoles.
A new fluoro-Wang resin is presented which facilitates solid-phase reaction monitoring using 19F NMR. The resin is easily synthesized and amenable to scale-up. The method described herein compliments single-bead FT-IR and 13C NMR techniques. This method allows monitoring of solid-phase reactions even if the resin bound intermediate is unstable to the cleavage conditions. In addition, this is a useful tool to study reaction kinetics on the solid phase.
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