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Directed ortho ‐Metalation of Aryl Amides, O‐ Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation
Author(s) -
Miah M. A. Jalil,
Sibi Mukund P.,
Chattopadhyay S.,
Familoni Oluwole B.,
Snieckus Victor
Publication year - 2018
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.201701143
Subject(s) - metalation , chemistry , electrophile , aryl , combinatorial chemistry , stereochemistry , competition (biology) , group (periodic table) , medicinal chemistry , organic chemistry , catalysis , ecology , alkyl , biology
A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt 2 , in comparison with the OCONEt 2 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.