Variability of Rhodium(III)-Catalyzed Reactions of Aromatic Oximes with Alkenes

Acetophenone oxime reacts with various alkenes in the presence of the rhodium catalyst [Cp*RhCl (2) ] (2) (2.5 mol%; Cp* = pentamethylcyclopentadienyl) and 1,1,1,3,3,3-hexafluoropropan-2-ol as an important cosolvent. Styrene, aliphatic terminal alkenes, and strained cyclic alkenes gave the correspon...

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Bibliographic Details
Published inSynlett Vol. 31; no. 11; pp. 1117 - 1120
Main Authors Trifonova, Evgeniya A., Komarova, Alina A., Chusov, Denis, Perekalin, Dmitry S.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
isoquinolines
C-H activation
ALLYLATION
ARENES
REGIOSELECTIVE SYNTHESIS
alkenes
oximes
rhodium catalysis
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Summary:Acetophenone oxime reacts with various alkenes in the presence of the rhodium catalyst [Cp*RhCl (2) ] (2) (2.5 mol%; Cp* = pentamethylcyclopentadienyl) and 1,1,1,3,3,3-hexafluoropropan-2-ol as an important cosolvent. Styrene, aliphatic terminal alkenes, and strained cyclic alkenes gave the corresponding substituted dihydroisoquinolines in yields of 50-99%. On the other hand, alkenes containing functional groups close to the double bond gave a variety of different products. The reactions of acetophenone oxime with styrene or dec-1-ene in the presence of the chiral catalyst [(C (5) H (2) (t) Bu (2) CH (2) (t) Bu)RhI (2) ] (2) provided the corresponding dihydroisoquinolines with improved regioselectivity but a low enantiomeric ratio (61:39 in both cases).
Bibliography:Russian Science Foundation
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1707961