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Regioselective Formal β-Allylation of Carbonyl Compounds Enabled by Cooperative Nickel and Photoredox Catalysis.

Title Regioselective Formal β-Allylation of Carbonyl Compounds Enabled by Cooperative Nickel and Photoredox Catalysis.
Authors Kun Liu, Zhe Wang, Augustinus N Künzel, Marcus Layh, Armido Studer
Magazine Angewandte Chemie (International ed. in English)
Date 09/11/2023
DOI 10.1002/anie.202303473
Introduction The Tsuji-Trost reaction is extensively employed in synthesising natural and pharmaceutical compounds, favouring α-allylation due to the acidity of the α-C-H bond. However, targeting β-allylation of carbonyl compounds poses a significant challenge due to its less acidic β-C-H bond. This study introduces a method for formal intermolecular β-C-C bond formation using diverse aldehydes and ketones with various allyl electrophiles through nickel and photoredox catalysis. Initial transformation of aldehydes and ketones into silyl enol ethers achieves β-selectivity. The process benefits from mild conditions, high regioselectivity, broad functional group tolerance, and efficiency. This approach enables access to valuable building blocks that are challenging to obtain with existing methods.
Quote Kun Liu, Zhe Wang and Augustinus N Künzel et al. Regioselective Formal β-Allylation of Carbonyl Compounds Enabled by Cooperative Nickel and Photoredox Catalysis. Angew. Chem. Int. Ed. Engl. 2023. Vol. 62(37). DOI: 10.1002/anie.202303473
Element Nickel (Ni)
Materials Chemical Compounds
Industry Chemical & Pharmacy
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