Blue Light Induced Difluoroalkylation of Alkynes and Alkenes

Abstract

The difluoroalkylation of alkynes and alkenes by direct photoexcitation of ethyl difluoroiodoacetate is described. Under catalyst- and oxidant-free conditions, iododifluoro­alkylation and hydrodifluoro­alkylation products were generated from alkynes, and difluoroalkylation products were prepared from alkenes. This methodology provides a streamlined access to difluoroalkylated organic compounds starting from simple alkynes or alkenes.

Progress in Visible Light‐Induced Difluroalkylation of Olefins

“…Visible‐light induced difluoroalkylation of alkenes by direct photoexcitation of ethyl difluoroiodoacetate was reported by Fan and co‐workers (Scheme 37a) [109] . Interestingly, this protocol worked under catalyst‐ and oxidant‐free conditions.…”

“…Visible-light induced difluoroalkylation of alkenes by direct photoexcitation of ethyl difluoroiodoacetate was reported by Fan and co-workers (Scheme 37a). [109] Interestingly, this protocol worked under catalyst-and oxidant-free conditions. It was found that the developed strategy selectively gave the difluoroalkylated and hydrodifluoroalkylation products from alkynes by the tuning the solvents (Scheme 37b).…”

Copper‐Catalyzed C−H Difluoroalkylation of Coumarins with Fluoroalkyl Bromides

“…[14] Copper-catalyzed CÀ H fluoroalkylation has been recognized as a powerful method to access complex fluorinated molecules and biomolecules. [15] On the other hand, direct CÀ H fluoroalkylation of coumarin derivatives by photoexcited catalysis, [16] palladium catalysis, [17] Rh(III) catalysis [18] and EDA complexes or halogen bond initiator [19] has proved to be capable for the post-modification of pharmaceutical significant molecules. Nevertheless, Cu-catalyzed CÀ H fluoroalkylation of heteroarenes, e. g. coumarin derivatives, has not been systematically investigated previously and the reaction yield was not satisfying (Scheme 2), [20] especially considering the appealing fact of utilizing fluoroalkylated heteroarenes as pharmacophores.…”

Visible-light Promoted Atom Transfer Radical Addition−Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-donor

“…The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a facile route for further application in pharmaceuticals and life sciences.Molecules 2020, 25, 508 2 of 8 mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity [52].…”

“…Molecules 2020, 25, 508 2 of 8 mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity [52].…”