兰州大学机构库 >化学化工学院
New Approaches for Biaryl-Based Phosphine Ligand Synthesis via P=O Directed C-H Functionalizations
Ma, YN; Li, SX; Yang, SD; 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.
收录类别SCIE ; PUBMED
2017-06
发表期刊ACCOUNTS OF CHEMICAL RESEARCH
卷号50期号:6页码:1480-1492
出版者AMER CHEMICAL SOC
出版地WASHINGTON
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
学科领域Chemistry
所属项目编号NSFC [21472076, 21532001] ; PCSIRT [IRT_15R28, lzujbky-2016-ct02]
资助项目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
DOI10.1021/acs.accounts.7b00167
ISSN0001-4842
文章类型Review
语种英语
WOS记录号WOS:000404085900022
PM记录号28485596
IR记录号WOS:000404085900022
第一机构
Citation statistics
???java.ItemTag.Counts???31[WOS]   ???java.ItemTag.WOS.Record???     ???java.ItemTag.WOS.Related-Records???
文献类型期刊论文
条目标识符http://ir.lzu.edu.cn/handle/262010/190172
Collection化学化工学院
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.
作者单位16CHEM
Recommended Citation:
GB/T 7714
Ma, YN,Li, SX,Yang, SD,et al. 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.
APA Ma, YN,Li, SX,Yang, SD,Yang, SD ,&Yang, SD .(2017).New Approaches for Biaryl-Based Phosphine Ligand Synthesis via P=O Directed C-H Functionalizations.ACCOUNTS OF CHEMICAL RESEARCH,50(6),1480-1492.
MLA Ma, YN,et al."New Approaches for Biaryl-Based Phosphine Ligand Synthesis via P=O Directed C-H Functionalizations".ACCOUNTS OF CHEMICAL RESEARCH 50.6(2017):1480-1492.
Files in This Item:
There are no files associated with this item.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Altmetrics Score
谷歌学术
谷歌学术Similar articles in Google Scholar
[Ma, YN]'s Articles
[Li, SX]'s Articles
[Yang, SD]'s Articles
百度学术
百度学术Similar articles in Google Scholar
[Ma, YN]'s Articles
[Li, SX]'s Articles
[Yang, SD]'s Articles
必应学术
必应学术Similar articles in Google Scholar
[Ma, YN]'s Articles
[Li, SX]'s Articles
[Yang, SD]'s Articles
Related Copyright Policies
Null
???item.sidebar.baidu.bookmark-share???
???jsp.display-item.all??? (0)
[???jsp.display-item.idea???]
???jsp.display-item.comment-text2???
Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.