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2.1.2.1.1.5 Arylboronic Acids/Esters (Chan–Lam–Evans Coupling)

DOI: 10.1055/sos-SD-208-00078

Hay, M. B.; Hicks, J. D.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132129.

Chan, Lam, and Evans pioneered the field of copper-mediated couplings of arylboronic acids with nitrogen nucleophiles.[‌28‌,‌29‌] Although the original methods for oxidative C—N coupling utilize stoichiometric copper, more recent developments have rendered the reaction catalytic through the use of oxygen as a terminal oxidant.[‌30‌,‌31‌] Couplings of primary aromatic amines with arylboronic acids are typically performed with a copper(II) salt such as copper(II) acetate in toluene or a halogenated solvent in the presence or absence of base. Molecular sieves are often added to remove water, preventing undesired phenol formation. Coupling typically occurs at room temperature, providing an advantage over standard cross-coupling methods for sensitive substrates.

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References