Thianthrenation-Enabled α-Arylation of Carbonyl Compounds with Arenes

Abstract

The Pd-catalyzed α-arylation of carbonyl compounds with simple arenes enabled by site-selective thianthrenation has been demonstrated. This one-pot process using thianthrenium salts as the traceless arylating reagents features mild conditions and a broad substrate scope. In addition, this protocol could also tolerate the heterocyclic carbonyl compounds and complex bioactive molecules, which is appealing for medicinal chemistry.

Photoredox-Catalyzed Dehydrogenative Csp3–Csp2 Cross-Coupling of Alkylarenes to Aldehydes in Flow

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.14 (d, J = 8.1 Hz, 2H), 7.09 (d, J = 8.1 Hz, 2H), 3.64 (s, 2H), 2.43 (t, J = 7.4 Hz, 2H), 2.34 (s, 3H), 1.56 (p, J = 7.4 Hz, 2H), 1.35–1.13 (m, 4H), 0.87 (t, J = 7.1 Hz, 3H); 13 C­{ 1 H} NMR (101 MHz) δ 209.0, 136.6, 131.5, 129.5, 129.4, 49.9, 42.0, 31.4, 23.6, 22.5, 21.2, 14.0. Spectroscopic data are consistent with those previously reported …”

TEMPO-mediated late stage photochemical hydroxylation of biaryl sulfonium salts

“…At the initial stage of the investigation, biphenyl was chosen as a substrate to form aryl thianthrenium [18][19][20][21][22][23][24] salt 2a, which was utilized to explore the optimal conditions for a siteselective hydroxylation of simple arenes (Table 1). The type of light, power, additive, reaction time, solvent and hydroxyl sources were notably evaluated.…”

Diverse C–P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C–S Bond Cleavage

“…Sulfonium salts have been attracting increasing attention owing to their broad applications in synthetic chemistry . Recently, arylsulfonium salts such as aryl-tetrafluoro­thianthrenium (Ar-TFT) salts, arylthianthrenium (Ar-TT) salts, and aryldibenzo­thiophenium (Ar-DBT) salts have been developed as a class of versatile electrophile reagents for various transformations by Ritter and others . An example of Michaelis–Arbuzov phosphonate synthesis using an Ar-TFT salt with triphenylphosphite (P­(OPh) 3 ) under photoredox catalysis has been reported; however, the reaction of any arylsulfonium salts with diarylphosphines (Ar 1 Ar 2 PH) is unprecedented to the best of our knowledge.…”