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 pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

主权项

1. A method of performing a chemical reaction, comprising:
reacting in a reaction mixture a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I):
R1—B-T   (I), where
R1 represents a 2-heterocyclic group or a cyclopropyl group,T represents a conformationally rigid protecting group,B represents boron having spa hybridization,a corresponding unprotected organoboronic acid is unstable by the boronic acid neat stability test, andthe reaction mixture further comprises a base having a pKB of at least 1, and a palladium catalyst; and forming a cross-coupled product in the reaction mixture.