The Role of Base in Reaction Performance of Photochemical Synthesis of Thiazoles: An Integrated Theoretical and Experimental Study

• Published in: Chemistry : a European journal Vol. 30; no. 26; pp. e202304279 - n/a
• Main Authors: Xu, Jiaxin, Ye, Xiaoyu, Lv, Zongchao, Chen, Yi‐Hung, Wang, Xiang Simon
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 08.05.2024
• Subjects: Artificial intelligence; Atmospheric chemistry; Chemical synthesis; Density Functional Theory; Machine Learning; Molecular structure; Organic chemistry; Photochemical reactions; Photochemicals; Photochemistry; Photoredox; Quantum chemistry; Reaction condition; Substrates; Thiazoles; Reaction condition; Machine Learning; Photoredox; Density Functional Theory
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202304279

Artificial intelligence (AI)/machine learning (ML) is emerging as pivotal in synthetic chemistry, offering revolutionary potential in retrosynthetic analysis, reaction conditions and reaction prediction. We have combined chemical descriptors, primarily based on Density Functional Theory (DFT) calculations, with various AI/ML tools such as Multi‐Layer Perceptron (MLP) and Random Forest (RF), to predict the synthesis of 2‐arylbenzothiazole in photoredox reactions. Significantly, our models underscore the critical role of the molecular structure and physicochemical characteristics of the base, especially the total atomic polarizabilities, in the rate‐determining steps involving cyclohexyl and phenethyl moieties of the substrate. Moreover, we validated our findings in articles through experimental studies. It showcases the power of AI/ML and quantum chemistry in shaping the future of organic chemistry. This work focuses on the prediction of the synthesis of 2‐arylbenzothiazole. Different AI/ML methods are then employed for model training and testing. Feature analysis is conducted through the model interpretation process, enabling further exploration into the reaction mechanisms. We then chose two substrates of distinct structures and verified the predictions through experimental benchwork. This represents a novel reaction with different bases.