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2.1.1.1.1.8 Copper-Catalyzed Coupling of Alkylamines with Boronic Acid Derivatives (Chan–Lam–Evans Reaction)

DOI: 10.1055/sos-SD-208-00002

Tomás-Gamasa, M.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013223.

The discovery of the copper-promoted Chan–Lam–Evans coupling reaction[‌51‌,‌52‌] in 1998 greatly enhanced carbon–heteroatom cross-coupling chemistry as it permits the replacement of the aryl halide partner with boronic acids. Nowadays, it is recognized as a powerful synthetic tool whose attractiveness is increasing due to the mild reaction conditions required (e.g., room temperature, weak base, and ambient atmosphere), the ready availability of boronic acids and their derivatives, and its high functional group tolerance.[‌53‌,‌54‌] Chan, Lam, and co-workers also demonstrated that arylboronic esters and triphenylboroxin can be used in place of arylboronic acids in the N-arylation reaction.[‌54‌]

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