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One-pot synthesis of trifluoromethylated phthalans via intramolecular cyclization from 2-alkynylbenzaldehydes
Authors:Lijun Xu  Haizhen Jiang  Jian Hao  Gang Zhao
Affiliation:1. Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
Abstract:An efficient tandem addition/cyclization procedure for the synthesis of trifluoromethylated phthalans under mild conditions was developed. This procedure involves tetrabutylammonium fluoride (TBAF)-promoted addition of Ruppert–Prakash reagent (TMSCF3) to 2-alkynylbenzaldehyde to give 2-alkynylbenzylicalcohols, which would then undergo base-catalyzed selective 5-exo-dig cyclization to furnish the corresponding products.
Keywords:Trifluoromethylation   Ruppert&ndash  Prakash reagent   Intramolecular cyclization   Tetrabutylammonium fluoride   2-Alkynylbenzaldehyde
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