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Name pinyin
YANG Zhiping
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081701 化学工程
Subject category of dissertation
08 工学
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Pd2(dba)3和手性双膦配体(R, R)-QuinoxP*催化下,以芳基次膦酸酯作为膦氢化试剂,实现了炔烃的不对称膦氢化反应,以28-94%产率和33-86%对映选择性合成具有磷手性的烯基次膦酸酯。根据单晶衍射确定产物的磷手性中心的绝对构型为R。根据氘代实验的结果,确定反应过程中氧化加成、炔烃的氢钯化和配体交换过程为可逆过程,提出可能的膦氢化反应机理:Pd2(dba)3(R, R)-QuinoxP*配位生成零价钯配合物,可能经过以下两种途径。Path A:零价钯配合物与二苯基次膦酸进行氧化加成得到钯氢物种;之后与炔烃发生氢钯化得到乙烯基钯中间体;与次膦酸酯进行配体交换后,再还原消除得到最终产物。Path B:零价钯配合物与次膦酸酯直接进行氧化加成得到钯氢物种;接着与炔烃发生氢钯化得到乙烯基钯中间体;最后还原消除得到产物。两条反应途径在反应过程中同时存在。



Other Abstract

Chiral phosphorus compounds have important application value and potential in pharmaceutical chemistry, organic synthetic chemistry and life sciences. Therefore, developing synthetic methodology of chiral phosphorus compounds is always a hotspot in organic synthesis. Asymmetric hydrofunctionalization, an important part of modern organic synthesis, is one of the most efficient protocols to prepare optically active compounds with the development of asymmetric catalysis. This dissertation focused on palladium-catalyzed asymmetric hydrophosphorylation of alkynes access to P-stereogenic phosphinates and hydrophosphinylation of allenes access to chiral allylic phosphine oxides, as well as enantioselective and regioselective hydroamination of cinnamyl phosphonic acid derivatives by copper-catalysis access to chiral γ-amino phosphonic acid derivatives.

Palladium-catalyzed asymmetric hydrophosphorylation of alkynes with arylphosphinates has been developed. A variety of chiral P-stereogenic phosphinates were obtained in 28-94% yields with 33-86% enantioselectivities by Pd2(dba)3 /(R, R)-QuinoxP* catalytic system. The absolute configuration of hydrophosphorylation product was unambiguously confirmed as R by X-ray crystallographic analysis. Based on the deuterium-labeling experiment, it proved that the oxidative addition, hydropalladation and ligand exchange were reversible. A possible mechanism was proposed in accordance with the deuterium-labeling experiment. Formation of chiral palladium complex is from Pd2(dba)3 and (R, R)-QuinoxP*. Path A: Subsequent oxidative addition of chiral palladium complex to Ph2P(O)OH produces Pd-H species. The hydropalladation of alkynes takes place to give an α-alkenylpalladium intermediate by Markovnikov addition. Subsequent ligand exchange with phosphinate and reductive elimination give the desired product. Path B: The intermediate Pd-H is generated directly by the oxidative addition of the P–H bond of phosphinates to palladium. Then hydropalladation of alkynes and reductive elimination give the desired alkenylphosphinate product. Both pathways exit at the same time in the reaction system.

Pd(PPh3)4/(R)-Difluorphos-catalyzed enantioselective hydrophosphinylation of allenes with diarylphosphine oxides is presented access to chiral allylic phosphine oxides in 50-99% yields with 79-99% enantioselectivities. The absolute configuration of the allylic phosphine oxides was determined to be R by single crystal X-ray analysis. This methodology was further applied in the first synthesis of chiral 2H-chromene by two-steps method and later stage functionalization of cholesterol derivative. A possible mechanism of hydrophosphinylation was proposed in the light of deuterium incorporation. Pd(PPh3)4 and (R)-Difluorphos generate chiral palladium complex. Subsequent coordination with allene gives a basic intermediate that can snatch up proton from phosphinous acid (diphenylphosphine oxide’s tautomeric form) to form allylpalladium intermediate. It then undergoes allylic substitution at the α-position, for positive charge stabilized by an alkoxy group, to give chiral allylic phosphine oxides and regenerate the chiral Pd complex.

Cu(OAc)2/(R)-DTBM-segphos-catalyzed enantioselective and regioselective hydroamination of cinnamyl phosphonic acid derivatives is proposed to achieve chiral γ-amino phosphonic acid derivatives in 52-90% yields with 69-99% enantioselectivities, as well as chiral δ-amino esters and δ-amino phosphonic acid derivatives in 37-40% yields with 98-99% enantioselectivities. The absolute configuration of amination product was determined to be S by the comparison with chiral product obtained by a two steps synthesis from (S)-3-amino-3-phenylpropan-1-ol. A protonation reaction by using CD3OD instead of hydroxylamine ester was conducted to probe the regioselectivity of the generated organocopper species to confirm the reaction mechanism. L*CuH is generated by reduction of Cu(OAc)2 and (R)-DTBM-segphos by methyldimethoxysilane (DMMS). L*CuH’s stereoselective migratory insertion into an alkene of cinnamyl phosphonic acid derivatives would generate an alkyl copper complex. Subsequent intramolecular SN2 cleavage of N-O linkage of the hydroxylamine ester followed by reductive elimination would give the hydroamination product. The left Cu(I) species would be reduced with DMMS to reform the L*CuH species .

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杨志萍. 钯、铜催化手性磷化合物的不对称合成研究[D]. 哈尔滨. 哈尔滨工业大学,2022.
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