期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 12, 期 9, 页码 1475-1487出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob42380h
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资金
- Region Bretagne
- Agence Nationale de la Recherche
- Institut Universitaire de France
- Rennes Metropole
1-Aryl-1H-benzotriazoles and -1H-indazoles were synthesized, and their deproto-metallation using the base prepared by mixing LiTMP with ZnCl2 center dot TMEDA (1/3 equiv.) was studied. In the indazole series, reactions occurring at the 3 position were followed by ring opening, and functionalization of the substrate was only found possible (on the sulfur ring) using 2-thienyl as aryl group. In the benzotriazole series, either mono- or bis-deprotonation (depending on the amount of base employed) was achieved with phenyl, 4-methoxyphenyl and 2-thienyl as aryl group, and bis-deprotonation in the case of 4-chlorophenyl and 4-trifluoromethylphenyl. The experimental results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method.
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