Photoredox α-Arylation of cyclic ketones

24 January 2022, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The direct α-arylation of unactivated carbonyl compounds using aryl halides represents a powerful method to synthesize criti-cal building blocks for diverse useful compounds. Numerous synthetic methods exist to forge C(sp2)-C(sp3) bonds, albeit metal free direct α-arylation of unactivated cyclic ketones has long been an elusive transformation. Herein, we report a green-light-mediated α-arylation of unactivated ketones from readily available aryl halides via activation of a C(sp2)-X bond (X=I, Br, Cl) and an α-carbonyl C(sp3)-H bond in a single photocatalytic cycle. This approach is characterized by its mild reaction conditions, operational simplicity, and wide functional group tolerance. Importantly, the impressive outcome from multi-gram photocatalytic reaction underpins the strength of this method as a potentially practical and attractive approach for scale-up industrial purposes. The utility and scope of this reaction were further demonstrated by new syntheses of several feedstock chemicals that are commercially expensive but critical for synthesizing numerous pharmaceutical agents.

Keywords

Photocatalysis
alpha-Arylation
Ketone
Green light
Large scale reaction
Acridinium

Supplementary materials

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Title
Supportive Information - Photoredox α-Arylation of Carbonyl Compounds
Description
This document contains the supporting information for the manuscript entitled - Photoredox α-Arylation of Carbonyl Compounds - and contains general information, catalyst synthesis and characterization, mechanistic investigation, experimental procedures, as well as NMR spectroscopy and X-ray data.
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