Publication Date:
2014-11-15
Description:
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.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Martinez-Martinez, Antonio J -- Kennedy, Alan R -- Mulvey, Robert E -- O'Hara, Charles T -- New York, N.Y. -- Science. 2014 Nov 14;346(6211):834-7. doi: 10.1126/science.1259662.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow G1 1XL, UK. ; WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow G1 1XL, UK. r.e.mulvey@strath.ac.uk charlie.ohara@strath.ac.uk.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/25395533" target="_blank"〉PubMed〈/a〉
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
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Chemistry and Pharmacology
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Computer Science
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Medicine
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Natural Sciences in General
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Physics
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