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Direct Organocatalytic Oxo‐Metathesis, a trans‐ Selective Carbocation‐Catalyzed Olefination of Aldehydes
Author(s) -
Bah Juho,
Franzén Johan
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403651
Subject(s) - chemistry , carbocation , metathesis , catalysis , electrophile , oxetane , cycloaddition , organic chemistry , reactivity (psychology) , lewis acids and bases , medicinal chemistry , polymerization , medicine , polymer , alternative medicine , pathology
A direct organocatalytic carbonyl/olefin oxo‐metathesis has been developed. The reaction is catalyzed by trityl tetrafluoroborate (TrBF 4 ) and utilizes unactivated alkenes for the olefination of aromatic aldehydes to give trans β‐alkylstyrenes in yields of 44–85 % with only acetone as the byproduct. The pronounced Lewis acidity of the carbocation results in unusual reactivity that is proposed to catalyze a stepwise [2+2] cycloaddition to give an oxetane intermediate. Fragmentation of the latter in a formal retro [2+2] reaction gives the oxo‐metathesis product.