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PHOTOREDOX Α-ARYLATION OF CYCLIC KETONES"

Nature Synthesis, 2022, 1, 147–157

The direct α-arylation of carbonyl compounds using aryl halides represents a powerful method to synthesize critical building blocks for diverse useful compounds. Numerous synthetic methods exist to forge C(sp2)–C(sp3) bonds although mild and metal-free direct α-arylation of ketones remains a challenging transformation. Here we report a green-light-mediated α-arylation of 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 of the multigram 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 formal syntheses of several feedstock chemicals that are commercially expensive but critical for synthesizing numerous pharmaceutical agents.

T. GIANETTI RECEIVED THE UA EARLY CAREER INNOVATION AND ENTREPRENEURSHIP AWARD 2022

March 25, 2022

The award honors an early career faculty member who as demonstrated significant involvement in expanding the impact of their research to the public good through innovation and commercialization.