Convergent dendron approach using a phenol triallyl building block: synthesis of a phenol dendron containing 27 allyl termini

Abstract

A successful convergent dendron synthesis is achieved using a phenol triallyl (AB3) building block by a sequence of reactions consisting of hydrosilylation-phenol protection. The key feature is the hydrosilylation using dimethylchloromethylsilane that avoids the side dehydrohalogenation previously found with linear branches containing β-hydrogens. The advantage of the AB3 building block is the multiplication of the dendron branches by three at each generation, which allows the synthesis of the second-generation 27-allyl phenol dendron.