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2.1.2.1.1.4.3 Aryl Methanesulfonates

DOI: 10.1055/sos-SD-208-00078

Hay, M. B.; Hicks, J. D.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132128.

Aryl methanesulfonates are the least reactive electrophiles for the amination of aromatic amines, although they possess several advantageous properties, including higher stability relative to other sulfonates and increased atom economy in cross-coupling reactions.[‌17‌,‌73‌] Aryl methanesulfonate aminations typically involve palladium catalysts derived from electron-rich phosphines such as BrettPhos (2) or related ligands and are carried out in the presence of weak bases in alcoholic solvents at elevated temperature (Scheme 22).[‌17‌,‌73‌] Under these conditions, the reaction is successful, providing products 37 for a variety of electronically diverse aryl methanesulfonates and amines and tolerates a variety of functional groups, including enolizable ketones.[‌17‌,‌73‌]

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