Direct Organocatalytic Oxo‐Metathesis, a  trans‐ Selective Carbocation‐Catalyzed Olefination of Aldehydes | Zendy

Bah Juho | Zendy; Franzén Johan | Zendy

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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.

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