Dual Function of N‑Iodosuccinimide for C(sp3)–B Bond Activation

A practical method for C­(sp3)–B bond activation was developed. Using a combination of alkyl trifluoroborates and N-iodosuccinimide (NIS), various C­(sp3)–heteroatom bonds were readily generated in an efficient manner. Mechanistic studies revealed the bifunctional ability of NIS: mediating the forma...

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Published inOrganic letters Vol. 26; no. 1; pp. 198 - 203
Main Authors Youn, Ju Hyun, Go, Su Yong, Chung, Hyunho, Lee, Haeyeon, Chung, Taek Dong, Cheong, Paul Ha-Yeon, Lee, Hong Geun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ACIDS
SECONDARY
CHEMISTRY
BORONIC ESTERS
GENERATION
OXIDATIVE AMINATION
EFFICIENT
TRANSFORMATIONS
C-H
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Summary:A practical method for C­(sp3)–B bond activation was developed. Using a combination of alkyl trifluoroborates and N-iodosuccinimide (NIS), various C­(sp3)–heteroatom bonds were readily generated in an efficient manner. Mechanistic studies revealed the bifunctional ability of NIS: mediating the formation of reactive halogenated intermediates and activating them via halogen bonding. This electrophilic activation of the reaction center enables the utilization of general heteroatom nucleophiles, which are used in a limited capacity in traditional 1,2-metalate rearrangements.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03728