Slow release of organoboronic acids in cross-coupling reactions

A method of performing a chemical reaction, comprising:

• deprotecting in a reaction mixture a protected organoboronic acid represented by formula (IV):
• where
• R1 represents a 2-heterocyclic group, wherein the 2-heterocyclic group is an optionally substituted 3- to 10-membered heterocyclic group comprising 1 to 3 heteroatoms selected from O, N, and S, and wherein one heteroatom is at the 2-position in the heterocyclic group,
• B represents boron having sp3 hybridization,
• R20, R21, R22, R23, and R24 independently are selected from the group consisting of hydrogen and an organic group, wherein the organic group is selected from the group consisting of an alkyl group, a heteroalkyl group, an alkenyl group, a heteroalkenyl group, an alkynyl group, a heteroalkynyl group, an aryl group, and a heteroaryl group, and
• the reaction mixture further comprises a base and a palladium catalyst,
• to form a corresponding unprotected organoboronic acid that is unstable by the boronic acid neat stability test;
• reacting in the reaction mixture the unprotected organoboronic acid and a compound selected from the group consisting of an organohalide and an organopseudohalide;
• and
• forming a cross-coupled product in the reaction mixture;
• where the time required for at least 90% of the protected organoboronic acid to be deprotected in the reaction mixture is at least equal to the time required for 90% of the cross-coupled product to be formed in the reaction mixture.