Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 4, Pages 447-454Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701143
Keywords
Metalation; Amides; Carbamates; Regioselectivity; Aromatic substitution
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Funding
- NSERC Canada
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A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the anionic ortho-Fries (AoF) rearrangement, the double metalation-electrophile quench of 1,2- and 1,4-O-carbamates, and iterative metalation procedures are presented. The results provide new methodologies for the synthesis of contiguously functionalized 1,2,3- and 1,2,3,4-substituted aromatic derivatives of difficult accessibility and potential broad utility. A comparison of the present methodology with previously developed routes is provided for selected examples with emphasis on such substituted compounds.
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