ヒドラゾン-パラジウム触媒によるアリル化合物を利用した分子変換反応

抄録

This review describes palladium-catalyzed reactions of allylic compounds via π-allyl-palladium intermediate using hydrazone ligand. Generally, phosphine-type ligands were utilized for palladium-catalyzed reaction of allylic compounds. We found that allylic arylation of allylic ester with aryl boronic acids proceeded smoothly at room temperature and afforded 1,3-diarylpropene derivatives using phosphine-free hydrazone-palladium catalyst system. Moreover, we demonstrated that allylic arylation of allylic aryl ether also proceeded smoothly using this catalyst system. Inspired from this reaction, we found hydrazone-palladium catalyzed one-molecular reaction of allyloxyphenylboronic acid derivatives bearing allylic aryl ether moiety and arylboronic acid moiety afforded the corresponding allylphenol derivatives. Furthermore, we demonstrated that hydrazone ligand was more effective than phosphine-type ligand for palladium-catalyzed annulation via coordinating of π-allyl-palladium intermediate to triple bond electrophilically.