6345-94-4Relevant academic research and scientific papers
Photoinduced C(sp3)-H chlorination of amides with tetrabutyl ammonium chloride
Zhu, Yanshuo,Yu, Wei
supporting information, p. 10228 - 10232 (2021/12/13)
A new protocol was developed for the site-selective C(sp3)-H chlorination of amides with tetrabutyl ammonium chloride as the chlorinating agent. The reaction features a tandem sequence that involves a (diacetoxyiodo)benzene-mediated and chloride anion-involved N-H chlorination followed by photoinitiated chlorine atom transfer. A wide variety of carboxamides and sulfonamides were chlorinated at the δ-position by using this method.
Photoinduced site-selective C(sp3)-H chlorination of aliphatic amides
Zhu, Yanshuo,Shi, Jingcheng,Yu, Wei
supporting information, p. 8899 - 8903 (2020/11/30)
Herein, we report a new photochemical method for C(sp3)-H chlorination of amides which employs tert-butyl hypochlorite as the chlorinating agent and a household compact fluorescent lamp as the light source. The reaction proceeds via N-heterocyclic carbene SIPr·HCl-promoted N-H chlorination and subsequent photoinduced Hofmann-L?ffler-Freytag chlorine atom transfer. The latter process is facilitated by (diacetoxyiodo)benzene. This protocol exhibits a broad scope and is suitable for site-selective chlorination of methyl hydrogen as well as methylene and methine hydrogen.
DECONSTRUCTIVE FUNCTIONALIZATION METHODS AND COMPOUNDS
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Paragraph 0464-0470, (2020/01/31)
Disclosed herein, inter alia, are deconstructive functionalization methods and compounds made using the same.
Halogenation of primary alcohols using a tetraethylammonium halide/[Et 2NSF2]BF4 combination
Pouliot, Marie-France,Mahe, Olivier,Hamel, Jean-Denys,Desroches, Justine,Paquin, Jean-Francois
supporting information, p. 5428 - 5431,4 (2020/10/15)
The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et2NSF2]BF4 (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.
