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Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2021-09-21 , DOI: 10.1002/adsc.202100607
Xingyu Chen 1 , Sixian Lu 2 , Ping Deng 3 , Xiaoqiang Chang 2 , Yifan Zhao 1 , Yue Ma 4 , Dong Zhang 4 , Fei Xia 1 , Lan Yang 2 , Jigang Wang 5 , Peng Sun 2
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A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance.

中文翻译:

路易斯酸调节醌亚胺缩酮 (QIK) 和 1,3-二羰基化合物之间的发散催化反应:可切换获取多种产品,包括 2-芳基-1,3-二羰基化合物、吲哚和苯并呋喃

醌亚胺缩酮 (QIKs) 和 1,3-二羰基化合物之间的催化路易斯酸调节反应为各种骨架提供了一种发散和可调的方法,包括一系列 2-芳基-1,3-二羰基化合物、吲哚和苯并呋喃。氯化锂和溴化亚铁的使用产生 QIK 的 C3-或 C2-烷基化产物。溴化亚铁和三氟甲磺酸的组合提供吲哚衍生物。在三氟甲磺酸镱 (III) 和化学计算量的水存在下发生顺序水解和 C3-烷基化。当用三氟甲磺酸和化学计算量的水进行反应时,得到苯并呋喃。该协议利用温和的条件,表现出区域和化学选择性,并具有广泛的官能团耐受性。
更新日期:2021-09-21
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