| First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation. | |
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MedLine Citation:
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PMID: 17391047 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78 degrees C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0 degrees C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1). |
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Authors:
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Thi-Huu Nguyen; Nguyet Trang Thanh Chau; Anne-Sophie Castanet; Kim Phi Phung Nguyen; Jacques Mortier |
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Publication Detail:
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Type: Journal Article Date: 2007-03-29 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Apr |
Date Detail:
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Created Date: 2007-04-20 Completed Date: 2007-06-29 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 3419-29 Citation Subset: - |
Affiliation:
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Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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