Diels–Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene S,S-dioxides: an unprecedented de-oxygenation vs. sulfur dioxide extrusion

Abstract

Diels-Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence...

Tf2O/2-Chloropyridine-Triggered Synthesis of Benzo[b]thiophene 1,1-Dioxides from Sulfonium α-Acyl Sulfonylmethylides

“…13 C{ 1 H} NMR (101 MHz, CDCl 3 ): δ 142. 7, 140.8, 140.7, 140.2, 137.1, 134.1, 133.9, 130.3, 129.52, 129.48, 129.1, 128.0, 127.6, 127.3, 123.5, 122.4, 21.5, 15.9 5,5,6,8,6,7,benzo [b]thiophene 1,1-Dioxide (2k dr = 1:1). Colorless crystals; yield: 42 mg (48%); Mp: 181−183 °C; R f = 0.50 (PE/EA 10:1, v/v).…”

“…6-Methyl-3-phenyl-2-thiocyanatobenzo [b]thiophene 1,1-Dioxide (7). Yellow crystals; yield: 46 mg (74%); Mp: 126−128 °C; R f = 0.51 (PE/EA 5:1, v/v).…”

“…2 Additionally, benzo [b]thiophene 1,1dioxides play a pivotal role as important building blocks in diverse organic synthesis, such as 1,3-dipolar cycloadditions, 3 asymmetric hydrogenations, 4 cross-dehydrogenative coupling, 5 enantioselective tandem sulfa-Michael/aldol reactions, 6 and deoxygenated/sulfur dioxide extruded Diels−Alder reactions. 7 Hence, developing novel and practical methods for functionalized benzo [b]thiophene 1,1-dioxides will be highly valuable.…”

“…Moreover, benzo­[ b ]­thiophene 1,1-dioxides possess the fascinating ability to serve as a novel class of luminogens, inducing aggregation-induced emission (AIE) and showcasing the ability to switch between absorbance and fluorescence (Figure ). Additionally, benzo­[ b ]­thiophene 1,1-dioxides play a pivotal role as important building blocks in diverse organic synthesis, such as 1,3-dipolar cycloadditions, asymmetric hydrogenations, cross-dehydrogenative coupling, enantioselective tandem sulfa-Michael/aldol reactions, and deoxygenated/sulfur dioxide extruded Diels–Alder reactions . Hence, developing novel and practical methods for functionalized benzo­[ b ]­thiophene 1,1-dioxides will be highly valuable.…”

Palladium-Catalyzed C2-Selective Oxidative Olefination of Benzo[b]thiophene 1,1-Dioxides with Styrenes and Acrylates

“…Traditional methods for the synthesis of thiophene 1,1-dioxides contain oxidation of thiophenes, , Diels–Alder reactions, and C–X/C–M (M = Sn and B) cross-couplings . Recently, transition-metal-catalyzed oxidative C–H activation has been one of the most powerful tools in organic synthesis .…”