A Palladium-Catalyzed Three-Component Synthesis of Arylmethylsulfonamides

Abstract

A palladium-catalyzed three-component synthesis of arylmethylsulfonamide derivatives from sulfonamides, paraformaldehyde, and arylboronic acids has been developed. The method is operationally simple and provides rapid access to a broad range of structurally interesting sulfonamidomethyl compounds.

Palladium-catalyzed asymmetric three-component reaction between glyoxylic acid, sulfonamides and arylboronic acids for the synthesis of α-arylglycine derivatives

“…First test reactions with our previously established Pd (TFA) 2 — S,S′-iPr Box-catalyst systems ( Beisel and Manolikakes. 2013 ; Beisel and Manolikakes, 2015 ; Beisel, Diehl and Manolikakes, 2016 ; Beisel and Manolikakes, 2016 ; Diehl and Manolikakes, 2020 ) led to highly interesting observations. In the presence of the palladium catalyst, the desired a -arylglycine (13a) was obtained in a decreased yield of 55%–65% under otherwise identical reaction conditions (MeNO 2 , 40°C for 16 h) ( Scheme 2B ).…”

“…Recently, we have disclosed palladium-catalyzed, three-component transformations between (sulfon) amides, different aldehyde components and boronic acids or carboxylic acids as broadly applicable alternatives to the classical Petasis reaction ( Beisel and Manolikakes. 2013 ; Beisel and Manolikakes, 2015 ; Beisel, Diehl and Manolikakes, 2016 ; Beisel and Manolikakes, 2016 ; Diehl and Manolikakes, 2020 ). With glyoxylic acid ester as aldehyde component, the corresponding a -arylglycines esters 8) can be obtained in high yields and enantioselectivities ( scheme 1c ) ( Beisel, Diehl and Manolikakes, 2016 ).…”