One-pot synthesis of trifluoromethylated phthalans via intramolecular cyclization from 2-alkynylbenzaldehydes

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• 作者：Lijun Xu^a ; Haizhen Jiang^a ; ^{hzjiang@shu.edu.cn" class="auth_mail} ; Jian Hao^a ; ^{jhao@shu.edu.cn" class="auth_mail} ; Gang Zhao^b ; ^{zhaog@mail.sioc.ac.cn" class="auth_mail}
• 关键词：Trifluoromethylation ; Ruppert&ndash ; Prakash reagent ; Intramolecular cyclization ; Tetrabutylammonium fluoride ; 2-Alkynylbenzaldehyde
• 刊名：Tetrahedron
• 出版年：22 July 2014
• 年：2014
• 卷：70
• 期：29
• 页码：4373-4378
• 全文大小：585 K

文摘

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.