中文版 | English
Title

Auto Machine Learning Assisted Preparation of Carboxylic Acid by TEMPO-Catalyzed Primary Alcohol Oxidation

Author
Corresponding AuthorRuan,Zhixiong; Liao,Kuangbiao
Publication Years
2022
DOI
Source Title
ISSN
1001-604X
EISSN
1614-7065
Abstract
Though alcohol oxidations were considered as well-established reactions, selecting productive conditions or predicting reaction yields for unseen alcohols remained as major challenges. Herein, an auto machine learning (ML) model for TEMPO-catalyzed oxidation of primary alcohols to the corresponding carboxylic acids is disclosed. A dataset of 3444 data, consisting of 282 primary alcohols and 45 conditions, were generated using high-throughput experimentation (HTE). With the HTE data and 105 descriptors, a multi-label prediction was performed with AutoGluon (an open-source auto machine learning framework) and KNIME (an open-source data analytics platform). For the independent test of 240 reactions (a full matrix of 20 unseen alcohols and 12 conditions), AutoGluon with multi-label prediction for yield prediction (AGMP) gave excellent performance. For external test of 1308 reactions (consisting of 84 alcohols and 45 conditions), AGMP still afforded good results with R as 0.767 and MAE as 4.9%. The model also revealed that the newly generated descriptor (Y/N, classification of the reaction reactivity) was the most relevant descriptor for yield prediction, offering a new perspective to integrate HTE and ML in organic synthesis.
Keywords
URL[Source Record]
Indexed By
Language
English
SUSTech Authorship
Others
Funding Project
National Natural Science Foundation of China[22071249]
WOS Research Area
Chemistry
WOS Subject
Chemistry, Multidisciplinary
WOS Accession No
WOS:000896969600001
Publisher
ESI Research Field
CHEMISTRY
Scopus EID
2-s2.0-85143272249
Data Source
Scopus
Citation statistics
Cited Times [WOS]:2
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/416548
DepartmentDepartment of Chemistry
Affiliation
1.Guangdong Laboratory Animals Monitoring Institute,Guangdong Provincial Key Laboratory of Laboratory Animals,Guangzhou,Guangdong,510663,China
2.Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology,the NMPA and State Key Laboratory of Respiratory Disease,School of Pharmaceutical Sciences and the Fifth Affiliated Hospital,Guangzhou Medical University,Guangzhou,Guangdong,511436,China
3.Bioland Laboratory,Guangzhou,Guangdong,510005,China
4.Department of Chemistry,Southern University of Science and Technology,Shenzhen,Guangdong,518055,China
5.Guangzhou Laboratory,Guangzhou,Guangdong,510320,China
Recommended Citation
GB/T 7714
Qiu,Jia,Xu,Yougen,Su,Shimin,et al. Auto Machine Learning Assisted Preparation of Carboxylic Acid by TEMPO-Catalyzed Primary Alcohol Oxidation[J]. CHINESE JOURNAL OF CHEMISTRY,2022.
APA
Qiu,Jia.,Xu,Yougen.,Su,Shimin.,Gao,Yadong.,Yu,Peiyuan.,...&Liao,Kuangbiao.(2022).Auto Machine Learning Assisted Preparation of Carboxylic Acid by TEMPO-Catalyzed Primary Alcohol Oxidation.CHINESE JOURNAL OF CHEMISTRY.
MLA
Qiu,Jia,et al."Auto Machine Learning Assisted Preparation of Carboxylic Acid by TEMPO-Catalyzed Primary Alcohol Oxidation".CHINESE JOURNAL OF CHEMISTRY (2022).
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