K₂S₂O₈‐Mediated Oxysulfonylation of Vinyl Azides with Sodium Sulfinates to Access β‐Keto Sulfones in Water

Abstract

With water as solvent, K2S2O8 mediated facile and efficient synthesis of β‐keto sulfones through oxysulfonylation of vinyl azides with sodium sulfinates is described. The novel procedure has the advantages of being environmentally benign, mild reaction conditions, short reaction time, easy and simple operation, wide tolerance of functional groups, which establish the practical application of this methodology.

Visible-Light-Driven Denitrogenative C–C Bond Formation and Oxidative Difunctionalization of Vinyl Azides

“…55 After that, intermediate VI was formed via two possible pathways: one is the H abstraction (a) of iminyl radical, another undergoes the SET (b), then H + abstraction of intermediate V. Finally, the radical intermediate VI undergoes hydrolysis to convert the intermediate into the final product -oxyalkylketones (products 3 and 5). [56][57][58][59] In summary, we are motivated by an initial design concept of exploring the direct synthesis of -oxyalkyl ketone from vinyl azides by combining the power of C-H functionalization and visible-light photocatalysis. 60 We have established a straightforward, versatile protocol and operated under mild reaction conditions.…”

Copper-catalyzed multicomponent cascade synthesis of polyfunctionalized β-ketone sulfones

“…Furthermore, vinyl azides can readily form β-ketone sulfones, β-carbolines and β-ketone phosphines when acting as radical acceptors and this provides a new pathway for the construction of structurally novel β-C(sp 3 )-H molecular frameworks. 7 In particular, β-ketone sulfones consists of three essential functional groups: sulfonyl, carbonyl and active methylene moieties (α-acid proton), enabling the further assembly of many intrinsically valuable carbocyclics and heterocyclics. 7d As expected, these compounds have attracted considerable attention due to their unique biological activities including antihepatitis, anti-bacterial, anti-fungal, and so on.…”