Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 9, Pages 1941-1951Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00236h
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Funding
- Spanish MICINN (SGPI) [CTQ2016-80913-P, PID2019-111406GB-I00]
- Junta de Castilla y Leon [VA224P20]
- UVa
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Functionalization of simple arenes is challenging, as it requires cleaving the sluggish C-H bond and overcoming the weak coordinating ability of the arene pi-system. Using a well-defined palladium complex with a specific ligand and a moderately coordinating solvent can decrease the amount of arene used, while a co-solvent like t-butyl methyl ketone can accelerate the reaction process by altering the concentration and stability of relevant metal species.
The functionalization of simple arenes without coordinating directing groups is a challenge. Besides facing the task of cleaving the sluggish C-H bond, the process is hampered by the weak coordinating ability of the arene pi-system to the metal, which results in reactions that need a large excess of the reactant arene. Using a well-defined palladium complex with the ligand [2,2 '-bipyridin]-6(1H)-one, we have found that the use of a moderately coordinating solvent allows a decrease of the amount of arene used. Moreover, for the least coordinating arenes, the co-solvent produces a significant accelerating effect by altering the concentration and relative stability of relevant metal species in the catalytic cycle as well as the catalyst resting state. t-Butyl methyl ketone (pinacolone) is one of the most effective co-solvents: Even if the ketone C-H bond cleaves easily, the final products are determined by the reductive elimination step (the product-forming step) so the target biaryl products are selectively observed.
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