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- Title
Practical and Selective sp<sup>3</sup> C−H Bond Chlorination via Aminium Radicals.
- Authors
McMillan, Alastair J.; Sieńkowska, Martyna; Di Lorenzo, Piero; Gransbury, Gemma K.; Chilton, Nicholas F.; Salamone, Michela; Ruffoni, Alessandro; Bietti, Massimo; Leonori, Daniele
- Abstract
The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine‐tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site‐selective chlorination of sp3 C−H bonds. This process exploits the ability of protonated N‐chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical‐chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H‐atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C−H chlorination.
- Subjects
CHLORINATION; RADICALS (Chemistry); AGRICULTURAL chemicals; CHLORINE; POLYMERS; WATER purification
- Publication
Angewandte Chemie, 2021, Vol 133, Issue 13, p7208
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202100030