Rhodium(II)-Catalyzed Hinsberg Dearomatization Using Trimethylsilyldiazomethane

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8083 - 8088

Published: Nov. 3, 2023

Rhodium(II) catalyzes carbene transfer from trimethylsilyldiazomethane to arylmethyl thioethers, generating sulfonium ylides that undergo [2,3]-sigmatropic rearrangement, punching quaternary centers into aromatic rings. The reaction works well with naphthalene, indole, and benzofuran ring systems, but the is unsuccessful monocyclic benzene homologue. For aryl Rh2(OAc)4 gives good results. alkyl yields improve Rh2(cap)4. Surprisingly, thioesters thiocarbamates are also competent substrates for reaction.

Language: Английский

Reactions with sulfoxonium ylides using metal-catalysis

Advances in organometallic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 227 - 286

Published: Jan. 1, 2024

Language: Английский