Directed ortho-meta'- and meta-meta'-dimetalations : a template base approach to deprotonation
Martínez-Martínez, Antonio J. and Kennedy, Alan R and Mulvey, Robert E and O'Hara, Charles T (2014) Directed ortho-meta'- and meta-meta'-dimetalations : a template base approach to deprotonation. Science, 346 (6211). pp. 834-837. ISSN 0036-8075 (https://doi.org/10.1126/science.1259662)
Preview |
PDF.
Filename: Martinez_etal_Science_2014_Directed_ortho_meta_and_meta_meta_dimetalations.pdf
Accepted Author Manuscript Download (1MB)| Preview |
Abstract
The regioselectivity of deprotonation reactions between arene substrates and basic metalating agents is usually governed by the electronic and/or coordinative characteristics of a directing group attached to the benzene ring. Generally, the reaction takes place in the ortho position, adjacent to the substituent. Here, we introduce a protocol by which the metalating agent, a disodium-monomagnesium alkyl-amide, forms a template that extends regioselectivity to more distant arene sites. Depending on the nature of the directing group, ortho-meta' or meta-meta' dimetalation is observed, in the latter case breaking the dogma of ortho metalation. This concept is elaborated through the characterization of both organometallic intermediates and electrophilically quenched products.
-
-
Item type: Article ID code: 50843 Dates: DateEvent14 November 2014Published3 October 2014AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 18 Dec 2014 14:44 Last modified: 18 Apr 2024 00:16 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/50843