-
E-mail
info@ika.cn
- Phone
-
Address
173-175 Youyi Road, Guangzhou Economic and Technological Development Zone
Aika (Guangzhou) Instrument Equipment Co., Ltd. (IKA/Aika, Germany)
Cover article of Green Chemistry: Professor Ruan Zhixiong's efficient synthesis of cyclic lactam compounds using electrochemical methods“
Date: 2021-12-27Read: 0
Cyclodextrin (8-11 membered ring) is an important medicinal chemical backbone, as it exists in many natural products and biologically active compounds, such as arbutin, rhamnosine, balazumab, and diphenylamine. Usually, these structures can only be obtained through limited methods such as intramolecular carbonylation, ring closure complex (RCM), Claisen type rearrangement, etc. A method for photocatalytic synthesis of cyclic lactam using transition metal ruthenium as catalyst and equivalent acetoxyphenyliodone (BI OAc) as oxidant has been reported recently. However, most of these methods are limited to using highly diluted solutions, transition metal catalysts, or equivalent chemical oxidants, which seriously deviates from the concept of green chemical synthesis.
Organic electrochemistry, which utilizes protons and electrons as redox reagents, has become an environmentally friendly, economical, and increasingly powerful green chemical synthesis method. As previously reported, direct or indirect electro oxidation of N-H bonds has been applied in various C-N bond cyclization reactions to construct N-containing heterocycles. Despite these significant advances, the reported methods rely on typical amide nitrogen radical cyclization reactions, i.e. electrochemical oxidation of C-N bond formation, to generate 5- or 6-membered rings. It has been proven that it is still difficult to form 8-11 membered cyclic lactams.
Recently, Professor Ruan Zhixiong's research group at Guangzhou Medical University developed a green and sustainable direct electrochemical oxidation method that generates amide nitrogen radicals without the need for catalysts and additional additives. The nitrogen radicals migrate through C-C bond cleavage,*A new breakthrough has been achieved in the ring expansion of 8-11 membered cyclic lactams(Green Chem., 2020, 22, 1099).
Compared with typical amide nitrogen radical cyclization methods in the past, this study used a graphite electrode as the working electrode (anode) and a platinum electrode as the cathode. Under milder and more environmentally friendly conditions such as room temperature and without the use of metal catalysts or external oxidants, the reaction was carried out at a constant current of 8 mA for 2.3 hours, successfully obtaining an 8-11 membered ring extension. As shown in the figure below, the yield of 9-membered ring intramolecular amide reached 98%.
At the end of the article, the author further unraveled the mystery of the reaction mechanism through cyclic voltammetry.
What equipment did Professor Ruan's research group use to complete and optimize the ring expansion reaction of cyclic lactams?! What equipment was used to achieve cyclic voltammetry?
Open the Supporting Information section of this article, which is the "IKA ElectraSyn pro". It can perform cyclic voltammetry analysis, as well as perform 6-position parallel screening simultaneously, optimize reaction conditions, and complete the reaction artifact.
With the artifact in hand, electrochemical synthesis achieves twice the result with half the effort!
[IKA Easter Egg]
The electrochemical synthesis method endorsed by various experts has been proven to be a new, green, economical, and potentially more promising approachMethod of formation. At present, the IKA "Electrochemical Synthesis Academic Exchange Group" has gathered over 200 domestic research experts and scholars to discuss and share together. Scan the code and start your journey of electrochemical synthesis!
Ruan Zhixiong, male, doctor, distinguished professor of Nanshan Scholar, young the Pearl River Scholar of Guangdong Province, master's supervisor and doctoral supervisor, doctor of Gottingen University, Germany, under the tutelage of * organic chemist Professor Lutz Ackermann. At present, we mainly engage in the design, synthesis, and activity research of new drug molecules, as well as research on green organic synthesis and catalytic methodology.
Source: Green Chemistry
About IKA
IKA is one of the professional manufacturers of laboratory instruments, analytical equipment, and processing technology in the industrial and scientific research fields. Headquartered in Stauffen, Germany, IKA's products and technical services serve over 160 customers. The company has over 900 employees dedicated to providing customers with good technology and helping them achieve success. At the same time, IKA also collaborates closely with universities and scientists to support its continuous exploration on the path of scientific research. In addition to its headquarters located in Germany, IKA now has wholly-owned subsidiaries operating independently in the United States, China, Malaysia, Japan, India, Brazil, South Korea, Vietnam, the United Kingdom, and Poland.
Last Article: Detection of COVID-19 virus by RT-PCR method