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

Qiu，Jia1,2,3; Xu，Yougen3; Su，Shimin3; Gao，Yadong3; Yu，Peiyuan4; Ruan，Zhixiong2; Liao，Kuangbiao1,3,5

2022

10.1002/cjoc.202200555

CHINESE JOURNAL OF CHEMISTRY   Impact Factor & Quartile

1001-604X

1614-7065

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.

AutoGluon Carboxylic acids Oxidation Primary alcohols TEMPO

SCI

English

Others

National Natural Science Foundation of China[22071249]

Chemistry

Chemistry, Multidisciplinary

WOS:000896969600001

WILEY-V C H VERLAG GMBH

CHEMISTRY

2-s2.0-85143272249

Scopus

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

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.

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.

Qiu，Jia,et al."Auto Machine Learning Assisted Preparation of Carboxylic Acid by TEMPO-Catalyzed Primary Alcohol Oxidation".CHINESE JOURNAL OF CHEMISTRY (2022).