Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 15, Pages 3222-3225Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905570
Keywords
annulation; electrosynthesis; medium-ring compounds; reduction; ring expansion
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Funding
- Deutsche Forschungsgemeinschaft [GRK2226]
- DFG [INST 184/108-1 FUGG]
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Cyclic alpha-(ortho-iodophenyl)-beta-oxoesters were converted in a ring-expanding transformation to furnish benzannulated cycloalkanone carboxylic esters. The reaction sequence started by electrochemical reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was adding to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon-carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of the reaction sequence was investigated by converting cyclic oxoesters with different ring sizes yielding benzocycloheptanone, -nonanone and -decanone derivatives in moderate to good yields. Furthermore, acyclic starting materials and cyclic compounds carrying additional substituents on the iodophenyl ring were submitted to this reaction sequence. The starting materials for this transformation are straightforwardly obtained by conversion of beta-oxoesters with phenyliodobis(trifluoroacetate).
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