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悉尼有机化学论文-二茂铁亚胺环钯化合物的合成、表征及其催化反应

论文作者:英语论文网论文属性:职称论文 Scholarship Papers登出时间:2012-02-20编辑:kalila点击率:3384

论文字数:6585论文编号:org201202201041452438语种:英语论文 English地区:澳大利亚价格:免费论文

关键词:二茂铁亚胺环钯化合物膦配体芳基卤晶体结构偶联反应

摘要:悉尼有机化学论文-二茂铁亚胺环钯化合物的合成、表征及其催化反应-Cyclopalladated Ferrocenylimines Complexes: Synthesis, Characterization and Application in C-C and C-N Coupling Reactions

悉尼有机化学论文-二茂铁亚胺环钯化合物的合成、表征及其催化反应-Cyclopalladated Ferrocenylimines Complexes: Synthesis, Characterization and Application in C-C and C-N Coupling Reactions-In this thesis, the synthesis, characterization and crystal structures of a series of newpyridine adducts, tricyclohexylphosphine adducts and monophosphinobiaryl ligand(DCPAB, DCPB) adducts of dimeric cyclopalladated ferrocenylimines were reported.

These complexes have been successfully used in palladium-catalyzed C-C and C-Nbond forming reactions of aryl bromides and aryl chlorides.1. Five new pyridine-cyclopalladated ferrocenylimine complexes 1-5 have been easilyprepared (Schemel) and well characterized by elemental analysis, ESI-MS, 1H NMRand IR spectra.

Their detailed structures are determined by single-crystal X-rayanalysis. To the best of our knowledge, the crystal structures of all monomeric imineand amine-based palladacycles indicate that, in the solid state, the trans isomercrystallizes preferentially. Surprisingly, the single crystal X-ray analysis of complex 2and 5 revealed cis-configuration of coordinated pyridine to the imino nitrogen in thesolid state, while 1, 3 and 4 are trans complexes. These complexes were found to beefficient for the Suzuki reaction of aryl bromides with phenylboronic acid.  http://www.51lunwen.org/australiathesis/  

Typically,using 0.2 mol% of 1 in the presence of 1.5 equivalent of K2CO3 as base in toluene at100℃could provide the coupled products in good to excellent yields.2. A series of new tricyclohexylphosphine(PCy3)-cyclopalladated ferrocenyliminescomplexes 6-11 have been easily synthesized (Scheme 2). The synthesis andcharacterization of a new 1,1’-bisferrocenylimine [{(η5-C5H4)-CH=NCy}2Fe] 12 and its monocyclopalladated derivative 14 were also reported (Scheme 3). The compound14 was found to be [PdCl{[(η5-C5H4)-CHO]Fe[(η5-C5H3)-CH=NCy]}(PCy3)], whichwas obtained from the reaction of 12 with equimolar amounts of Li2PdCl4/NaOAc inmethanol at room temperature and subsequent treatment of the resulting product withtricyclohexylphosphine (PCy3). The detailed structures of seven new palladacycleshave been determined by single-crystal X-ray analysis. The use of these palladacycles6-10 and 14 as catalysts for Suzuki and Heck reactions was examined.

They werefound to be very efficient for the Suzuki reaction of aryl chlorides with phenylboronicacid. Typically, using 0.1 mol% of catalyst in the presence of 1.5 equivalent ofCs2CO3 as base in dioxane at 100℃provided coupled products in excellent yields.These complexes also displayed good activity in the Heck reaction of a range of arylbromides with acrylic acid ethyl ester although they were not particularly useful forthe activation of aryl chlorides.3. One-pot synthesis of symmetrical biaryls via the coupling of bis(pinacolato)-diboron with aryl chlorides catalyzed by tricyclohexylphosphine-cyclopalladatedferrocenylimine complexes has been described (Scheme 4). These complexes werehighly effective catalysts and the typical catalytic loadings were 0.5-1mol%, whichwere rather low compared to the value of 4 mol% in the PdCl2(dppf) catalyzedcoupling of aryl bromides. The corresponding symmetrical biaryls were isolated in good to high yields.4. A series of new monophosphinobiaryl ligand (DCPB and DCPAB)-cyclopalladatedferrocenylimines complexes 16-25 have been easily synthesized (Scheme 5).

Thedetailed structures of six new palladacycles 16-17, 20, 22-23, 25 have beendetermined by 论文英语论文网提供整理,提供论文代写英语论文代写代写论文代写英语论文代写留学生论文代写英文论文留学生论文代写相关核心关键词搜索。

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