Dialkyl oxalates undergo selective diarylation on one of their carbonyl carbons upon treatment with arylboron reagents in the presence of a rhodium catalyst to give the corresponding alpha-hydroxydiarylacetates. Under similar conditions, the arylation of benzoylformate and benzil also proceeds efficiently.
Addition reactions O 0060Rhodium-Catalyzed Addition of Arylboron Compounds to Nitriles, Ketones, and Imines. -The rhodium-catalyzed intramolecular phenylation of nitriles, ketones and unactivated imines can be performed efficiently with sodium tetraphenylborate (I).Arylboronic acids such as (IV) can also be used as aryl sources, but they are less effective than the borate. Depending on the substrate used, the addition of H2O, CsF, or NH 4 Cl is crucial for smooth reactions. -(UEURA, K.; MIYAMURA, S.; SATOH*, T.; MIURA, M.; J.
General R 0010
Rhodium-Catalyzed Regioselective Arylation of Phenylazoles and Related Compounds with Arylboron Reagents via C-H BondCleavage. -Ethyl chloroacetate and KF act as a hydrogen acceptor and a promoter, respectively. -(MIYAMURA, S.; TSURUGI, H.; SATOH*, T.; MIURA, M.; J.
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