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题名: New Approaches for Biaryl-Based Phosphine Ligand Synthesis via P=O Directed C-H Functionalizations
作者: Ma, YN; Li, SX; Yang, SD
收录类别: SCIE ; PUBMED
出版日期: 2017-06
刊名: ACCOUNTS OF CHEMICAL RESEARCH
卷号: 50, 期号:6, 页码:1480-1492
出版者: AMER CHEMICAL SOC
出版地: WASHINGTON
英文摘要: CONSPECTUS: Given the important influence of phosphine ligands in transition metal-catalyzed reactions, chemists have searched for straightforward and efficient methodologies for the synthesis of diverse phosphine ligands. Although significant progress has been made in this aspect over the past decades, the development of new phosphorus-containing ligands with properties superior to their predecessors remains a central task for chemists. Recently, researchers have demonstrated that biphenyl monophosphine ligands function as highly efficient ligands for transition-metal-catalyzed organic transformations, especially for reactions where chelating bisphosphine ligands cannot be used. In 1998, Buchwald introduced a new class of air-stable phosphine ligands based on the dialkylbiaryl phosphine backbone. These ligands have been successfully used for a wide variety of palladium-catalyzed carbon carbon, carbon nitrogen, and carbon oxygen construction processes as well as serving as supporting ligands for a number of other reactions. At the same time, the use of the biphenyl monophosphine ligands often allows reactions to proceed with short reaction times and low catalyst loadings and under mild reaction conditions. However, the synthesis of chiral biphenyl monophosphine ligands, especially those the chirality of which is due to biaryl axial chirality, is very limited. In this Account, we summarize our methodologies for the synthesis of this kind of biphenyl monophosphine ligands including the P=O directed C-H functionalization, P=O directed diastereoselective C-H functiorialization, P=O directed enantioselective C-H functionalization, and metal-free diastereoselective radical oxidative C-H amination under mild reaction conditions. With these methods, a series of biphenyl phosphine ligand precursors containing achiral or axially chiral centers and precursors possessing both axial chirality and a chirogenic phosphorus center with different electronic properties and steric effect have been obtained under different reaction conditions. For the preparation of chiral biphenyl monophosphine ligands, which not only possess axial chirality but in many cases also possess chirality at phosphorus, the primary means of introducing chirality is through the use of the menthyl phenylphosphinate. As a chiral auxiliary group, the menthyl phenylphosphinate has some unique features: (i) it is easy to prepare; (ii) the products contain both axial chirality and central chirality on the phosphorus atom; (iii) the menthyl group could easily be transformed into other functional groups, which is crucial for the diversity of the corresponding biphenyl ligands. In our reaction, the P=O group not only acts as the directing group but also facilitates the construction of the phosphine ligands. In addition, the application of these products in asymmetric catalysis has also been studied with good results obtained in some reactions. The further application of these ligands, especially the chiral biphenyl monophosphine ligands in catalysis reactions is underway in our laboratory, and we hope different kinds of reactions will be achieved with these ligands.
作者部门: [Ma, Yan-Na ; Li, Shi-Xia ; Yang, Shang-Dong] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China ; [Yang, Shang-Dong] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
通讯作者: Yang, SD (reprint author), Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China. ; Yang, SD (reprint author), Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China.
学科分类: Chemistry
文章类型: Review
所属项目编号: NSFC [21472076, 21532001] ; PCSIRT [IRT_15R28, lzujbky-2016-ct02]
所属项目名称: 国家自然科学基金项目 ; 长江学者和创新团队发展计划 ; 中央高校基本科研业务费专项资金
项目资助者: NSFC ; MOE ; LZU
语种: 英语
DOI: 10.1021/acs.accounts.7b00167
ISSN号: 0001-4842
WOS记录号: WOS:000404085900022
PM记录号: 28485596
IR记录号: WOS:000404085900022
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内容类型: 期刊论文
URI标识: http://ir.lzu.edu.cn/handle/262010/190172
Appears in Collections:化学化工学院_期刊论文

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作者单位: 16CHEM

Recommended Citation:
Ma, YN,Li, SX,Yang, SD. New Approaches for Biaryl-Based Phosphine Ligand Synthesis via P=O Directed C-H Functionalizations[J]. ACCOUNTS OF CHEMICAL RESEARCH,2017,50(6):1480-1492.
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