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Silver Tetrafluoroborate‐Catalyzed Oxa‐Diels–Alder Reaction Between Electrically Neutral Dienes and Aldehydes
Author(s) -
Zou Xiaodong,
Yang Lizheng,
Liu Xiangli,
Sun Hao,
Lu Hongjian
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500487
Subject(s) - chemistry , chemoselectivity , regioselectivity , heteroatom , tetrafluoroborate , catalysis , diels–alder reaction , reactivity (psychology) , aryl , organic chemistry , medicinal chemistry , photochemistry , alkyl , ionic liquid , medicine , alternative medicine , pathology
Chemoselective oxa‐Diels–Alder reactions between electrically neutral 1,3‐dienes and various aldehydes were achieved using the commercially available silver tetrafluoroborate (AgBF 4 ) 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.