通过末端炔烃与缩醛的金介导反应合成炔丙基醚

Synthesis of Propargylic Ethers by Gold-Mediated Reaction of Terminal Alkynes with Acetals.

作者信息

Furuta Miyu, Sugiyama Kyoko, Yamaguchi Minami, Ueda Hirofumi, Tokuyama Hidetoshi

机构信息

Graduate School of Pharmaceutical Sciences, Tohoku University.

出版信息

Chem Pharm Bull (Tokyo). 2019;67(8):872-876. doi: 10.1248/cpb.c19-00322.

DOI:10.1248/cpb.c19-00322

PMID:31366835

Abstract

A gold-catalyzed introduction of various terminal alkynes to acetals was investigated. Extensive optimization of the reaction conditions revealed that thermally stable cationic gold catalysts bearing bulky ligands such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 3-1H-benzo[d][1,2,3]triazolyl gold trifluoromethanesulfonate (IPrAu(BTZ-H)OTf) were particularly suitable for the reaction. Additionally, significant solvent effects were observed. Ether solvents such as tetrahydrofuran (THF), cyclo pentyl methyl ether (CPME), and 1,4-dioxane were effective for the reaction. Studies on the scope of substrates and alkynes indicated that various alkynes and acetals were feasible to provide a wide range of propargylic ethers.

摘要

研究了金催化各种末端炔烃与缩醛的反应。对反应条件进行了广泛优化，结果表明，带有大位阻配体的热稳定阳离子金催化剂，如1,3-双(2,6-二异丙基苯基)咪唑-2-亚基三氟甲磺酸3-1H-苯并[d][1,2,3]三唑基金(IPrAu(BTZ-H)OTf)，特别适合该反应。此外，还观察到显著的溶剂效应。醚类溶剂如四氢呋喃(THF)、环戊基甲基醚(CPME)和1,4-二氧六环对该反应有效。对底物和炔烃范围的研究表明，各种炔烃和缩醛都能生成多种炔丙基醚。