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Silver Tetrafluoroborate-Catalyzed Oxa-Diels–Alder Reaction Between Electrically Neutral Dienes and Aldehydes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2015-10-13 05:10:35 , DOI: 10.1002/adsc.201500487
Xiaodong Zou , Lizheng Yang , Xiangli Liu , Hao Sun , Hongjian Lu

Chemoselective oxa-Diels–Alder reactions between electrically neutral 1,3-dienes and various aldehydes were achieved using the commercially available silver tetrafluoroborate (AgBF4) as catalyst. This catalytic process has high functional group tolerance. Heteroatoms at the β-position of the aryl aldehydes can greatly promote the reactivity of the substrates even with heterocyclic aldehydes that were previously believed to be unreactive for the oxa-Diels–Alder reaction. In addition, acroleins with β-heteroatom substitution are also good substrates. High chemoselectivity and regioselectivity were achieved at room temperature for the oxa-Diels–Alder reaction between acroleins and stoichiometric simple 1,3-dienes.

中文翻译:

四氟硼酸银催化的电中性二烯与醛之间的Oxa-Diels-Alder反应

使用市售的四氟硼酸银(AgBF 4)作为催化剂,可以实现电中性1,3-二烯与各种醛之间的化学选择性oxa-Diels-Alder反应。该催化过程具有较高的官能团耐受性。即使以前认为杂环醛对oxa-Diels-Alder反应没有反应性,芳基醛的β-位上的杂原子也可以极大地提高底物的反应性。另外,具有β-杂原子取代的丙烯醛也是良好的底物。室温下,丙烯醛与化学计量简单的1,3-二烯之间的oxa-Diels-Alder反应实现了高化学选择性和区域选择性。
更新日期:2015-10-14
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