Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Abstract

Herein, we present a (NH4)2S2O8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis of various phosphorothioate‐containing quinoxalin‐2(1H)‐one derivatives (46 examples) in 37‐79% yields. The reaction is compatible with a range of functional groups and is easily adaptable to large‐scale synthesis. Preliminary studies suggest the involvement of phosphorothioate radicals in these transformations.

Visible-Light Photoredox-Catalyzed Difunctionalization of Alkynes with Quinoxalin-2(1H)-Ones, P4S10, and Alcohols

“…Difunctionalization of alkynes with simultaneous introduction of two functional groups into organic framework have been emerged as an attractive strategy for the synthesis of various substituted vinyl compounds in terms of their atom- and step-economic advantages. − Quinoxalin-2­(1 H )-ones are important structural moieties present in various natural products and biologically active molecules, which have attracted considerable synthetic interest owing to their diverse chemical profile and biological activities. − Recently, some quinoxalin-2­(1 H )-one-containing vinyl compounds have been synthesized through difunctionalization of alkynes (Scheme a–c), − including three-component trifluoromethylheteroaromatization of alkynes with quinoxalin-2­(1 H )-ones and CF 3 SO 2 Na or trifluoromethyl thianthrenium triflate (TT-CF 3 + OTf – ), difunctionalization of alkynes with quinoxalin-2­(1 H )-ones and sulfonyl reagents, and difunctionalization of alkynes with quinoxalin-2­(1 H )-ones and AgSCF 3 . Although encouraging progress has been made in this area, the development of new difunctionalization of alkynes for forging other important quinoxalin-2­(1 H )-one-containing vinyl compounds is still highly demanded in synthetic and medicinal chemistry.…”