Slow release of organoboronic acids in cross-coupling reactions

摘要

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R¹—B-T  (I);where R¹ represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp³ hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pK_B of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.