An In‐Situ‐Formed Copper‐Based Perfluorinated Catalytic System for the Aerobic Oxidation of Alcohols

Abstract

Herein, we report a new catalytic protocol for the aerobic oxidation of alcohols. The catalytic system is formed in situ, in a straightforward and user‐friendly manner, combining a widely available copper source (Cu2O) with one imidazolium salt precursor bearing perfluorinated moieties. Our protocol uses TEMPO, as additive, and the reaction takes place at the interface of a biphasic solvent system, consisting of anisole and 1‐bromoperfluorooctane. The as‐prepared carbonyl compounds remain in the organic solvent, while the catalytic system remains in the fluorous phase. In this manner, the isolation and purification of the desired products are quite facile. Our protocol uses low catalytic loadings and is more efficient with primary alcohols, affording the desired products in good to excellent yields. The fluorous phase containing the catalytic system can be efficiently recovered and reused for at least six times, without a significant decrease in its catalytic efficiency.

Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines

“…To the best of our knowledge, the synthesis of thiazolidin-2-imines via a one-pot, multicomponent strategy, from readily available primary amines, ketones, terminal alkynes, and isothiocyanates, without the necessity of isolating the corresponding α-secondary propargylamines bearing quaternary carbon centers adjacent to the nitrogen atom and the alkyne group, has not been reported thus far. Upon adoption of a multicomponent strategy, the overall synthetic steps required to furnish these products are minimized, therefore promoting atom economy, reduction of waste, and reduction of the overall time and cost required for the entire synthetic endeavor. , Our continuous interest in the design and development of catalytic protocols promoting atom economy, use of low-cost and nontoxic metal sources, in low catalyst loadings, toward invaluable and biologically relevant compounds, in an efficient and simple synthetic manner, prompted us to develop an efficient and user-friendly protocol for the synthesis of these thiazolidin-2-imines, via a one-pot sequence, employing commercially available starting materials, as well as low-cost and low-toxicity transition state metal catalysts.…”

“…Upon adoption of a multicomponent strategy, the overall synthetic steps required to furnish these products are minimized, therefore promoting atom economy, reduction of waste, and reduction of the overall time and cost required for the entire synthetic endeavor. 9b , 17 Our continuous interest in the design and development of catalytic protocols promoting atom economy, use of low-cost and nontoxic metal sources, in low catalyst loadings, toward invaluable and biologically relevant compounds, in an efficient and simple synthetic manner, 18 prompted us to develop an efficient and user-friendly protocol for the synthesis of these thiazolidin-2-imines, via a one-pot sequence, employing commercially available starting materials, as well as low-cost and low-toxicity transition state metal catalysts.…”