The use of carboxylic acids as traceless directing groups for regioselective C–H bond functionalisation
Chemical Communications Pub Date: 2017-04-28 DOI: 10.1039/C7CC01755C
Abstract
The ability to selectively functionalise a specific C–H bond is a long-standing challenge due to the ubiquity of such bonds in organic molecules. One of the most common approaches to overcome this obstacle consists of installing directing groups into substrates to direct the functionalisation towards the desired C–H bond, leaving behind the directing group in the molecule. Alternatively, carboxylic acids have been employed as traceless directing groups that are easily removed after carboxylic acid-directed installation of the desired functionality. This review focuses on the development of this concept and its application to organic synthesis during the last decade.
Recommended Literature
- [1] Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China? Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing LiFood Funct., 2018,9, 4234-4245 10.1039/C8FO00787J
- [2] Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies Jason WanLab Chip, 2020,20, 4528-4538 10.1039/D0LC00881H
- [3] Distinct impact of glycation towards the aggregation and toxicity of murine and human amyloid-β? Eunju Nam,Jiyeon Han,Sunhee Choi,Mi Hee LimChem. Commun., 2021,57, 7637-7640 10.1039/D1CC02695J
- [4] Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR? Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing XiaNanoscale, 2020,12, 20456-20466 10.1039/D0NR04995F
- [5] Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)– Chem. Commun., 1998, 1501-1502 10.1039/A801804I
- [6] Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents Craig A. Kelly,David R. RosseinskyPhys. Chem. Chem. Phys., 2001,3, 2086-2090 10.1039/B010092G
- [7] Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides? Amandine Altmayer-Henzien,Valérie Declerck,David J. Aitken,Ewen Lescop,Denis Merlet,Jonathan FarjonOrg. Biomol. Chem., 2013,11, 7611-7615 10.1039/C3OB41876F
- [8] Fast synthesis of red Li3BaSrLn3(WO4)8:Eu3+ phosphors for white LEDs under near-UV excitation by a microwave-assisted solid state reaction method and photoluminescence studies Bo Wei,Zhenyu Liu,Chen Xie,Shu Yang,Wentao Tang,Aiwei Gu,Wing-Tak Wong,Ka-Leung WongJ. Mater. Chem. C, 2015,3, 12322-12327 10.1039/C5TC03165F
- [9] Fe3O4/Au/Fe3O4 nanoflowers exhibiting tunable saturation magnetization and enhanced bioconjugation Feng Shi,Kunping Yan,Mingli Peng,Xiao Cheng,Yanling Luo,Xuemei Chen,V. A. L. Roy,Zuankai WangNanoscale, 2012,4, 747-751 10.1039/C2NR11489E
- [10] Excellent lithium ion storage property of porous MnCo2O4 nanorods? Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen FangRSC Adv., 2016,6, 23074-23084 10.1039/C5RA26176G
Journal Name：Chemical Communications
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)