Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation
Xie, Shasha1; Li, Defang1,2; Huang, Hanchu1; Zhang, Fuyuan1,2; Chen, Yiyun1,2
2019-10-16
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume141Issue:41Pages:16237-16242
DOI10.1021/jacs.9b09099
AbstractThe intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to aketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.
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Indexed BySCI
Language英语
Funding ProjectStrategic Priority Research Program of the Chinese Academy of Sciences[XDB20020200]
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000491220300010
PublisherAMER CHEMICAL SOC
EISSN1520-5126
WOS KeywordALPHA-KETO ACIDS ; C-H ALKYLATION ; TITANIUM TRICHLORIDE ; PHENYLBORONIC ACID ; CARBONYL CARBON ; ONE-ELECTRON ; COMPLEXATION ; PHOTOREDOX ; MECHANISM ; ALKYNYLATION
Original Document TypeArticle
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Cited Times [WOS]:0   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://kms.shanghaitech.edu.cn/handle/2MSLDSTB/80514
Collection物质科学与技术学院_博士生
物质科学与技术学院_特聘教授组_陈以昀组
物质科学与技术学院_硕士生
Corresponding AuthorChen, Yiyun
Affiliation1.Univ Chinese Acad Sci, Chinese Acad Sci, State Key Lab Bioorgan & Nat Prod Chem, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
2.ShanghaiTech Univ, Sch Phys Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China
Corresponding Author AffilicationSchool of Physical Science and Technology
Recommended Citation
GB/T 7714
Xie, Shasha,Li, Defang,Huang, Hanchu,et al. Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2019,141(41):16237-16242.
APA Xie, Shasha,Li, Defang,Huang, Hanchu,Zhang, Fuyuan,&Chen, Yiyun.(2019).Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,141(41),16237-16242.
MLA Xie, Shasha,et al."Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 141.41(2019):16237-16242.
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