Ir-catalyzed Syntheses of Donor-Acceptor π-ConjugatedEnamines and Their Photoluminescence Properties

摘要

Enamines are useful synthetic intermediates as enolate equivalents in organic chemistry.Potential of enamines as electron donors have lately attracted considerable attention fromapplied physicists,and application of"π-conjugated enamines"(enamines stabilized byaromatic rings) into electronic devices such as hall transport materials were investigated.Twoefficient pathways for the syntheses of enamines were previously reported from our researchgroup.Hydrosilane reduction of N,N-dialkylcarboxamides into the corresponding aldenaminescatalyzed by Vaska's complex 1X was first developed.1 Preparation of π-conjugatedaldenamines from N,N-diarylcarboxamides was also achieved by using Vaska-type iridiumcomplex 1Y bearing electron-withdrawing perfluoroarylphosphite P(OC6F5)3,although 1Xshowed no catalytic activity toward the same reaction.2 We herein report catalytic hydrosilanereduction of carboxamides bearing electron-withdrawing groups using iridium complexes 1Xand 1Y,which leads to the formation of donor--acceptor conjugated enamines.