Regioselective and Stereospedfic Cross-Coupling of Primary Allylic Amines with Boronic Adds and Boronates through Palladium-Catalyzed C-N Bond Cleavage

摘要

The cross-coupling of allylic electrophiles with boronic acids and boronates is extremely useful for the formation of C-C bonds and for the introduction of the allyl moieties to target compounds. Allylic hahdes, esters, carbonates, phosphates,' and alcohols have been identified as allylic electrophiles with significantly different reactivity and selectivity. It is noteworthy that the employment of an allylic alcohol as the allylic electrophile is very attractive with respect to atom economy because the leaving OH group has a mass of 17 amu, which is much smaller than that of a halo or an OR (R/H) group. Nevertheless, the couphng of an α-chiral allylic alcohol with a boronic acid has been reported to afford a racemic product. To our knowledge, a leaving group with a mass smaller than 17 amu has not yet been reported for the coupling of an allylic electrophile with an organoboron.