Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

Abstract

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Photocatalytic Biheterocyclization of 1,7-Diynes for Accessing Skeletally Diverse Tricyclic 2-Pyranones

“…Visible light photoredox catalysis (VLPC) has evolved as an attractive and powerful synthetic strategy in the organic community, benefitting from the fascinating features of good functional group compatibility, availability, and safety as well as sustainability . Consequently, a great number of seminal reports have demonstrated the significant applicability of VLPC reactions in synthetic chemistry, making it more versatile and workable . Most existing photocatalytic transformations can be classified into the following reaction categories: [2 + 2] cycloadditions, α-functionalization of carbonyls or amines, dehalogenation reactions, radical C–H functionalizations of arenes, and redox-neutral annulations .…”

One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes

“…In addition, no changes were observed in the band maximum of the emission spectra with the increase in the isomer concentration ( Figure 1 A). 30 Surprisingly, no changes on the emission decay traces were observed by excitation of the Cu/BINAP complex at 445 nm, revealing a static fluorescence mechanism quenching 31 due a potential binding interaction between the Cu complex and the boronic ester in the ground state ( Figure 1 B). A similar behavior was observed when quenching studies were performed with the corresponding anti-isomer E - 2a with k q = 1.16 × 10 12 M –1 s –1 ( Figure 1 C, see Supporting Information for details), suggesting that Cu/BINAP and both isomers of boronic ester 2a can interact in the ground state, ruling out the possibility of quenching between the singlet excited state (S 1 ) of the Cu/BINAP complex and model substrate 2a .…”

CuCl-photocatalyzed C–H amination of benzoxazoles

“…On the other hand, the application of inexpensive Cu-complexes with long-lived excited states as photocatalysts in organic transformations is an attractive alternative to the conventionally used Ru-/Ir-complexes. 10 Based on our long-term research on photocatalysis, 11 we herein disclose that the simple CuCl can be used as a photocatalyst in the visible-light-induced amination of benzoxazoles with amines under mild conditions. With this photocatalytic procedure, various 2-aminobenzoxazoles were smoothly synthesized under an air atmosphere at room temperature (Scheme 1d).…”