Accessing 2-(Hetero)arylmethyl- -allyl-and -propargyl-21-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplingsof 2-(Chloromethyl)-21-borazaronaphthalenes

摘要

The synthesis of 2-(chloromethyl)-2,1-borazaronaphthalene has provided an opportunity to expand dramatically the functionalization of the azaborines. This azaborinyl building block can serve as the electrophile in palladium-catalyzed cross-coupling reactions to form sp³–sp and sp³–sp² bonds. The cross-coupling reactions of 2-(chloromethyl)-2,1-borazaronaphthalene with potassium (hetero)aryl- and alkenyltrifluoroborates as well as terminal alkynes provides access to a variety of novel azaborines, allowing a library of pseudobenzylic substituted azaborines to be prepared from one common starting material.