Selective photoredox direct arylations of aryl bromides in water in a microfluidic reactor?
Organic & Biomolecular Chemistry Pub Date: 2021-03-15 DOI: 10.1039/D1OB00050K
Abstract
Carrying out photoredox direct arylation couplings between aryl halides and aryls in aqueous solutions of surfactants enables unprecedented selectivity with respect to the competing dehalogenation process, thanks to the partition coefficient of the selected sacrificial base. The use of a microfluidic reactor dramatically improves the reaction time, without eroding the yields and selectivity. The design of a metal free sensitizer, which also acts as the surfactant, sizeably improves the overall sustainability of arylation reactions and obviates the need for troublesome purification from traces of metal catalysts. The generality of the method is investigated over a range of halides carrying a selection of electron withdrawing and electron donating substituents.
Recommended Literature
- [1] An alternative biorefinery approach to address microalgal seasonality: blending with spent coffee grounds Andre Prates Pereira,Tao Dong,Eric P. Knoshaug,Nick Nagle,Ryan Spiller,Bonnie Panczak,Christopher J. Chuck,Philip T. PienkosSustainable Energy Fuels, 2020,4, 3400-3408 10.1039/D0SE00164C
- [2] Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode Analyst, 1996,121, 1123-1126 10.1039/AN9962101123
- [3] An investigation on the interaction modes of a single-strand DNA aptamer and RBP4 protein: a molecular dynamic simulations approach? Raheleh Torabi,Hedayatollah Ghourchian,Massoud AmanlouOrg. Biomol. Chem., 2016,14, 8141-8153 10.1039/C6OB01094F
- [4] An antioxidant self-healing hydrogel for 3D cell cultures? Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei TaoJ. Mater. Chem. B, 2020,8, 1383-1388 10.1039/C9TB02792K
- [5] An integrated cathode and solid electrolyte via in situ polymerization with significantly reduced interface resistance? Jialiang Yuan,Ran Dong,Yuan Li,Yang Liu,Zhuo Zheng,Yuxia Liu,Yan Sun,Benhe Zhong,Zhenguo Wu,Xiaodong GuoChem. Commun., 2021,57, 13004-13007 10.1039/D1CC04485K
- [6] An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid? Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis NayakNew J. Chem., 2019,43, 4867-4877 10.1039/C9NJ00138G
- [7] An investigation on the second-order nonlinear optical response of cationic bipyridine or phenanthroline iridium(iii) complexes bearing cyclometallated 2-phenylpyridines with a triphenylamine substituent? David B. Cordes,Alexandra M. Z. Slawin,Stefania Righetto,Denis Jacquemin,Eli Zysman-Colman,Véronique GuerchaisDalton Trans., 2018,47, 8292-8300 10.1039/C8DT00754C
- [8] An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting? Lab Chip, 2019,19, 524-535 10.1039/C8LC01170B
- [9] An all-solid-state asymmetric device based on a polyaniline hydrogel for a high energy flexible supercapacitor? Hamid Heydari,Mohammad B. GholivandNew J. Chem., 2017,41, 237-244 10.1039/C6NJ02266A
- [10] Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties? S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. LeeRSC Adv., 2014,4, 23107-23115 10.1039/C4RA02318H
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.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)