Rhodium-catalyzed modification of phthalocyanines

Rhodium-catalyzed carbon–carbon bond forming reactions using phthalocyanine-boronate ester were investigated. The reaction of Pc-boronate ester with substituted aldehydes gave 1,2-addition products (secondary alcohols), while α,β-unsaturated carbonyl compounds (aldehydes, ketones, esters, and amides) furnished 1,4-addition products. The reaction of Pc-substituted alkynes with o-formyl and acetyl phenylboronic acid gave 1H- and 1-methyl inden-1-ol annulation derivatives. All reactions were performed in mixtures of organic–aqueous solvents.