中文版 | English
Title

Selective functionalization of hindered meta-C–H bond of o-alkylaryl ketones promoted by automation and deep learning

Author
Corresponding AuthorYang,Yuedong; Liao,Kuangbiao
Publication Years
2022-12-08
DOI
Source Title
ISSN
2451-9308
EISSN
2451-9294
Volume8Issue:12Pages:3275-3287
Abstract
Selective functionalization of the sterically hindered aromatic meta-C–H bond is unprecedented and remains to be a major challenge. Promoted by automation-based high-throughput experimentation (HTE) and deep learning (DL), a novel strategy to functionalize the hindered meta-C–H bond is disclosed. With carbon dioxide as a traceless director, a one-pot three-step protocol was developed to achieve selective arylation of o-alkylaryl ketones at the hindered meta position. This novel strategy involved photo-induced C–H carboxylation, carboxyl group-directed Pd-catalyzed C–H functionalization, and microwave-assisted decarboxylation. With HTE and DL, a broad scope of substrates was explored (1,032 reactions) and a DL-based model (CMPRY) for reaction yield prediction was established. Two independent tests with unseen o-alkylaryl ketones and/or potassium aryltrifluoroborates were used to evaluate the model. The model gave excellent performances in predicting unseen reactions; mean absolute errors in yield were only 6.6% and 8.4%, suggesting its potential in synthetic application.
Keywords
URL[Source Record]
Indexed By
Language
English
SUSTech Authorship
Others
Funding Project
National Natural Science Foundation of China[22071249];
WOS Accession No
WOS:000906065300001
Scopus EID
2-s2.0-85143980160
Data Source
Scopus
Citation statistics
Cited Times [WOS]:5
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/560324
DepartmentDepartment of Chemistry
Affiliation
1.Guangzhou Laboratory,Guangzhou,Guangdong,510320,China
2.Bioland Laboratory,Guangzhou,Guangdong,510005,China
3.School of Computer Science and Engineering,Sun Yat-sen University,Guangzhou,510006,China
4.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
Recommended Citation
GB/T 7714
Qiu,Jia,Xie,Jiancong,Su,Shimin,等. Selective functionalization of hindered meta-C–H bond of o-alkylaryl ketones promoted by automation and deep learning[J]. Chem,2022,8(12):3275-3287.
APA
Qiu,Jia.,Xie,Jiancong.,Su,Shimin.,Gao,Yadong.,Meng,Han.,...&Liao,Kuangbiao.(2022).Selective functionalization of hindered meta-C–H bond of o-alkylaryl ketones promoted by automation and deep learning.Chem,8(12),3275-3287.
MLA
Qiu,Jia,et al."Selective functionalization of hindered meta-C–H bond of o-alkylaryl ketones promoted by automation and deep learning".Chem 8.12(2022):3275-3287.
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