scholarly journals Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 251-257 ◽  
Author(s):  
Antoine Nitelet ◽  
Vanessa Kairouz ◽  
Hélène Lebel ◽  
André Charette ◽  
Gwilherm Evano

A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the double bond geometry. The reaction time was reduced by a factor of 24–48 compared to the batch process.

2020 ◽  
Author(s):  
Cristian Cavedon ◽  
Eric T. Sletten ◽  
Amiera Madani ◽  
Olaf Niemeyer ◽  
Peter H. Seeberger ◽  
...  

Protecting groups are key in the synthesis of complex molecules such as carbohydrates to distinguish functional groups of similar reactivity. The harsh conditions required to cleave stable benzyl ether protective groups are not compatible with many other protective and functional groups. The mild, visible light-mediated debenzylation disclosed here renders benzyl ethers orthogonal protective groups. Key to success is the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as stoichiometric or catalytic photooxidant such that benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time for this transformation can be reduced from hours to minutes in continuous flow. <br>


Author(s):  
Lais S. D. Azevedo ◽  
Anderson R. Aguillon ◽  
Marcelo T. Lima ◽  
Raquel A. C. Leão ◽  
Rodrigo O. M. A. de Souza

Author(s):  
Xiaojun Wei ◽  
Stephen V. Kershaw ◽  
Xiaodan Huang ◽  
Mingxia Jiao ◽  
Chau Chun Beh ◽  
...  

Author(s):  
Carsten J. Schmiegel ◽  
Patrik Berg ◽  
Franziska Obst ◽  
Roland Schoch ◽  
Dietmar Appelhans ◽  
...  

Author(s):  
Paolo Zardi ◽  
Michele Maggini ◽  
Tommaso Carofiglio

AbstractThe post-functionalization of porphyrins through the bromination in β position of the pyrrolic rings is a relevant transformation because the resulting bromoderivatives are useful synthons to covalently link a variety of chemical architectures to a porphyrin ring. However, single bromination of porphyrins is a challenging reaction for the abundancy of reactive β-pyrrolic positions in the aromatic macrocycle. We herein report a synthetic procedure for the efficient preparation of 2-bromo-5,10,15,20-tetraphenylporphyrin (1) under continuous flow conditions. The use of flow technology allows to reach an accurate control over critical reaction parameters such as temperature and reaction time. Furthermore, by performing the optimization process through a statistical DoE (Design of Experiment) approach, these parameters could be properly adjusted with a limited number of experiments. This process led us to a better understanding of the relevant factors that govern porphyrins monobromination and to obtain compound 1 with an unprecedent 80% yield.


2021 ◽  
Vol 27 (18) ◽  
pp. 5653-5657 ◽  
Author(s):  
Andreas Simoens ◽  
Thomas Scattolin ◽  
Thibault Cauwenbergh ◽  
Gianmarco Pisanò ◽  
Catherine S. J. Cazin ◽  
...  

2021 ◽  
pp. 2101616
Author(s):  
Iñigo Torres ◽  
Marta Alcaraz ◽  
Roger Sanchis‐Gual ◽  
Jose A. Carrasco ◽  
Michael Fickert ◽  
...  

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 303
Author(s):  
András Gy. Németh ◽  
Renáta Szabó ◽  
György Orsy ◽  
István M. Mándity ◽  
György M. Keserű ◽  
...  

We have developed the continuous-flow synthesis of thioureas in a multicomponent reaction starting from isocyanides, amidines, or amines and sulfur. The aqueous polysulfide solution enabled the application of sulfur under homogeneous and mild conditions. The crystallized products were isolated by simple filtration after the removal of the co-solvent, and the sulfur retained in the mother liquid. Presenting a wide range of thioureas synthesized by this procedure confirms the utility of the convenient continuous-flow application of sulfur.


2020 ◽  
Vol 02 (03) ◽  
pp. e128-e132
Author(s):  
Shao-Zheng Guo ◽  
Zhi-Qun Yu ◽  
Wei-Ke Su

AbstractThe development of highly efficient C–C bond formation methods for the synthesis of ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-(dimethylamino)acrylate 1 in continuous flow processes has been described, which is based on the concept of rapid and efficient activation of carboxylic acid. 2,4-Dichloro-5-fluorobenzoic acid is rapidly converted into highly reactive 2,4-dichloro-5-fluorobenzoyl chloride by treating with inexpensive and less-toxic solid bis(trichloromethyl)carbonate. And then it rapidly reacts with ethyl 3-(dimethylamino)acrylate to afford the desired 1. This process can be performed under mild conditions. Compared with the traditional tank reactor process, less raw material consumption, higher product yield, less reaction time, higher operation safety ensured by more the environmentally friendly procedure, and process continuity are achieved in the continuous-flow system.


2020 ◽  
Vol 59 (21) ◽  
pp. 8123-8127 ◽  
Author(s):  
Francesco Carraro ◽  
Jason D. Williams ◽  
Mercedes Linares‐Moreau ◽  
Chiara Parise ◽  
Weibin Liang ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document