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Study On The Suzuki Coupling Of NaBPh4 And Coupling Reaction Of Terminal Alkynes With Aroyl Chlorides Under Microwave Irradiation

Posted on:2002-08-04Degree:MasterType:Thesis
Country:ChinaCandidate:B G WeiFull Text:PDF
GTID:2121360032953338Subject:Applied Organic Chemistry
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The coupling reactions catalyzed by metal compounds are one of themost attractive areas for organic synthesis. In recent years, it is a veryeffective method for formation of C-C, C-N, C-B, C-S bonds. Recently, avariety of metal compounds have been applied to catalyze the couplingreactions. Its performance of catalysis is high activity and good selectivity.At present the coupling reaction of organoboranes with terminal olermes-.acid chlorides Aryl halides play an important role in internationalorganoboranes chemistry. This reaction has been applied to prepare thecompounds with saturated or unsaurated bonds. In addition, it is used tosynthesis the natural products.. bioactive compounds and chiral compounds.The study destination of this thesis is to probe into the metal compoundscatalyzed coupling reaction of sodium tetraphenylborate (NaBPht) withterminal olefines.. acid chlorides.. Aryl halides and terminal alkynes with acidchlorides under microwave irradiation condition. The coupling reaction oforganoboranes under microwave irradiation was firstly reported. Weobtained substituted olefines-. mono-substituted biphenyl ketones, mono-substituted biphenyl.. z,Jkunsaturated acetylenic ketones and obtained asimple.. rapid and high selective method for Suzuki's coupling reaction oforganoboranes. We broaden the scope of the microwave technology inorganometallic catalyzed reaction. We also firstly study the C-N couplingreaction of halohydrocarbon with ten amine and obtained the satisfactionalresult.This thesis includes four parts:Charpt one: The advance of solid phase organic synthesis under5microwave irradiation.We introduced the new advance of the microwave promoted organicsynthesis. We emphased on the organic reaction of polymer resin boundreatant .~. inorganic compounds doped reatant and solvent-free undermicrowave irradiation conditions. There are eight kinds of reactant patterns.In this chapter including alkylation .~ oxidation .~ condensationrearrangement aug so on. The application of microwave accelerated organicreaction in organic synthesis has been reviewed.Chapter two: study on palladium-catalyzed Suzuki coupling reaction ofsodium tetraphenylborate with terminal olefines acid chlorides, aryl halidesunder microwave irradiation condition.Microwave technology has been applied to many orangic reactions. Butthere ware a few reports about the metal-catalyzed reactions undermicrowave irradiation. The microwave-assisted coupling reaction oforganobranes has not been reported up to now. In this chapter, we firstlyaccomplished the coupling reaction of sodium tetraphenylborate withterminal olefmes.. acid chlorides and aryl halides catalyzed by Pd(II)-complex under microwave or microwaveè…œTC conditions, and there arethree subsections in this chapter.In first subsection, the Suzuki coupling reaction of sodium tetra-phenylborate with terminal oleflnes have been investigated in the presence ofPd(PPh3)2C12/AgNO3 under microwave irradiation and obtained theexcellent yield coupling products. We also present a propable reactionmechanism according to the literatures and experiment. In the experiment,taking the coupling of NaBPh4 with styrene as example, we investigated theinfluence of catalyst, reaction ratio., microwave power and time on the yields.Therefore, the better reaction conditions were selected. During the6experiment, we also studied the traditional terminal heating couplingreaction, and we found that microwave-assisted reaction get the rateincreased 60?00 times as that of the former conditions. This method issimple .~. fast and affords good yield.In second subsection, microwave assisted Suzuki coupling reaction ofNaBPh4 with aroyl chlorides catalyzed by Pd(PPh3)2C12 have been firstly...
Keywords/Search Tags:NaBPh4
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