Catalytic Enantioselective Construction of Chiral Benzo-Fused N -Heterocycles through Friedel–Crafts-Type Electrophilic Chlorination

Asymmetric Intermolecular Iodinative Difunctionalization of Allylic Sulfonamides Enabled by Organosulfide Catalysis: Modular Entry to Iodinated Chiral Molecules

“…Asymmetric Lewis basic chalcogenide catalysis has been paid much attention in recent years. − It has emerged as a powerful tool for asymmetric electrophilic functionalization of unsaturated compounds, especially alkenes. Elegant studies reported by Denmark, , Yeung, , and others , have demonstrated this catalysis for asymmetric sulfenylation and bromination of alkenes to produce a variety of chiral molecules.…”

“…Elegant studies reported by Denmark, , Yeung, , and others , have demonstrated this catalysis for asymmetric sulfenylation and bromination of alkenes to produce a variety of chiral molecules. Our group has also been working on this field and developed indane-based chiral chalcogenide catalysts for asymmetric electrophilic sulfenylation and chlorination of alkenes . We reasoned that these catalysts might be suitable for enantioselective iodination of alkenes under proper reaction conditions due to the great potentials of chalcogenide catalysis.…”

Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source

“…Benzo-fused saturated N -heterocycles are valuable motifs of biologically active natural alkaloids and in the manufacture of many drugs . Specifically, 1,2,3,4-tetrahydroquinoxaline stands out as one of the most significant compounds exhibiting great potential of applications in pharmaceutical, agro-chemical, and fine-chemical industries .…”

Chiral Chalcogenide-Catalyzed Enantioselective Electrophilic Hydrothiolation of Alkenes

“…In recent years, our group has been working on chalcogenide-catalyzed electrophilic reactions. 9,10,14 We discovered that Lewis basic chiral bifunctional chalcogenides could serve as a catalyst to activate electrophiles and transfer E + ions to alkenes to form a chiral cyclic onium ion intermediate. When the intermediate was relatively stable, it could react with weak nucleophiles to give chiral products.…”

“…In recent years, our group has been working on chalcogenide-catalyzed electrophilic reactions. ,, We discovered that Lewis basic chiral bifunctional chalcogenides could serve as a catalyst to activate electrophiles and transfer E + ions to alkenes to form a chiral cyclic onium ion intermediate. When the intermediate was relatively stable, it could react with weak nucleophiles to give chiral products. , Inspired by these discoveries, we hypothesized that if the transfer of the sulfenyl cation to alkenes was fast enough, the thiiranium ion intermediates would be formed and then give the desired sulfides without quenching the sulfenyl cation by challenging nucleophiles such as hydrides.…”