Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases

A general strategy for organocatalytic activation of C-H bonds via photoredox catalysis: direct arylation of benzylic ethers.

Direct C-H functionalization and arylation of benzyl ethers has been accomplished via photoredox organocatalysis. The productive merger of a thiol catalyst and a commercially available iridium photoredox catalyst in the presence of household light directly affords benzylic arylation products in good to excellent yield. The utility of this methodology is further demonstrated in direct arylation ...

Pd-catalyzed oxidative coupling of arene C-H bonds with benzylic ethers as acyl equivalents.

A palladium-catalyzed oxidative coupling of arene C-H bonds with benzylic ethers via C-H bond activation is described. The reaction proceeds efficiently with a broad range of substrates bearing conventional directing groups with excellent functional group compatibility. This protocol potentially provides opportunities to use dibenzyl ethers as new acyl equivalents for catalytic acylation reacti...

Direct β-functionalization of cyclic ketones with aryl ketones via the merger of photoredox and organocatalysis.

The direct β-coupling of cyclic ketones with aryl ketones has been achieved via the synergistic combination of photoredox catalysis and organocatalysis. Diaryl oxymethyl or aryl-alkyl oxymethyl radicals, transiently generated via single-electron reduction of ketone precursors, readily merge with β-enaminyl radical species, generated by photon-induced enamine oxidation, to produce γ-hydroxyketon...

Catalytic Enantioselective Carbon-Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C-H Bonds.

Benzylic alcohols and ethers are common subunits in bioactive molecules, as well as useful intermediates in organic chemistry. In this Communication, we describe a new approach to the enantioselective synthesis of benzylic ethers through the chiral phosphine-catalyzed coupling of two readily available partners, γ-aryl-substituted alkynoates and alcohols, under mild conditions. In this process, ...

The direct arylation of allylic sp3 C–H bonds via organocatalysis and photoredox catalysis