Study On The Cross-coupling Reaction Of Iridium Catalyzed Indole Derivatives

Indole derivatives constitute a significantly important class of nitrogen heterocyclic compounds.Given its unique structure and biological activity,they play a critically important role in many areas,such as medicines,pesticides,perfumes,dyes and functional materials.Since its discovery,enormous efforts have been devoted to the development of ever more efficient synthetic protocols for the preparation and direct founctionalization of these compounds.With the development of society,green and atom economic reactions have been strongly advocated.Developing environmentally friendly and high efficiency strategy has become a target pursued by many chemists.On the other hand,hydrogen evolution and transfer hydrogenative cross-coupling reactions are widely recognized as one of the most important strategies in organic synthesis.As they do not require pre-functionalization of the substrates,less reaction steps are needed coupled with no need for additional oxidants make it one of the most economical synthetic strategies in organic synthesis.Our team has been focusing on the synthesis and derivatization of nitrogen-containing heterocycles,On the basis of this background,this thesis presents the iridium-catalyzed hydrogen-evolution and transfer hydrogenative cross-coupling reactions catalysed by iridium.This thesis composes of following two sections:In the first section,by cooperative actions of iridium catalyst and NaOTf additive,a new direct access to nitrogen bi-heteroarenes via hydrogen-evolution cross-coupling of the?-site of indoles/pyrrole with the?-site of N-heteroarenes is described.The reaction proceeds in an atom-and redox-economic fashion together with the merits of an easily available catalyst system,broad substrate scope,excellent functional tolerance and no need for external oxidants,offering a practical way to create?-conjugated systems.In the second section,an iridium-catalysed hydrogen transfer strategy,enabling straightforward access to tetrahydro pyridine derivatives from aryl-1,8-naphthyridines and indolines is presented.This unprecedented synthetic protocol proceeds with the metris of high step-and economic fashion,no need for external compressed H₂ gas and no generation by-products,thus offering an important basis for the transformation of simple N-heterocycles into functionalized products.In summary,we have successfully achieved the reaction of indole derivatives and six-menmbered nitrogen heterocyclic by transfer hydrogenative and hydrogen evolution cross-coupling,which are further supplied a simle and effective way for the synthesis of biological molecules containing indole and prridine ring.