Application Of Highly Efficient Catalyst In The C-O(S), C-C Forming Reactions

The transition-metal catalyzed C-O(S), C-C bond formations are the fundamentalreactions in organic synthesis, which became the most popular topics. These protocolshave been substantially modified and developed over the past30years, providing anindispensable and simple methodology for preparative organic chemists. Based on thepioneering works on various cross-coupling reactions, herein, the formations of C-O(S),C-C bonds and their applications in organic synthesis have been studied.There are three chapters in this dissertation:The first chapter is about the ligand-free Fe/Cu co-catalyzed C-O(S) bondformation reactions. The study mainly focuses on the coupling reaction of aryl halidesincluding aryl iodides and bromides with various phenols, and thiophenols withoutusing ligand in the presence of the low-cost, benign and easily available Fe-Cu catalyst.Features of this protocol worth noting include the high selectivity of formation ofdisubstituted products, and the low amount of catalyst.The second chapter is about highly effective palladium-catalyzed Heck-typecouplings of hypervalent iodine reagents. Heck reaction has become an extremelyimportant organic synthesis method to build the C-C bond. When we study the Heckreaction, we find that we can use iodosodiacetate as arylation reagents, which is a goodcomplement to Heck reaction substrates. And the reaction is carried out under mildconditions, and low-toxicity PEG as the solvent, and also can be recycled for manytimes.The third chapter is about highly effective copper-catalyzed decarboxylativecoupling of aryl halides with alkynyl carboxylic acids. Pd has been widely used in thedecarboxylation-coupling reaction of the acetylenic acid compounds. However, thecheap Cu source is rarely used as a catalyst for the catalytic type of reaction. Therefore,we developed a highly efficient copper-catalyzed decarboxylation-coupling reaction between halides and alkyne acids. It is worth mentioning that our protocol can also beapplied for some aliphatic substrate.