Document Detail


Palladium-Catalyzed Mono-N-Allylation of Unprotected Anthranilic Acids with Allylic Alcohols in Aqueous Media.
MedLine Citation:
PMID:  21919524     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Palladium-catalyzed N-allylation of anthranilic acids 1a-j with allyl alcohol 2a in the presence of Pd(OAc)2, sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) in THF:H2O at room temperature gave only mono-N-allylated anthranilic acids 3a-j in good yields (70-98%). The reactions of 4-bromoanthranilic acid 1i with 2-methyl-3-buten-2-ol 2b showed complete chemoselectivity in N-allylation (neutral conditions) and C-vinylation (basic conditions). In our catalytic system, the keys to success are use of an unprotected anthranilic acid as a starting material and the presence of water in the reaction medium. The carboxyl group of anthranilic acid and water may play important roles for the smooth generation of the π-allyl palladium species by activation of the hydroxyl group of the allylic alcohol.
Authors:
Hidemasa Hikawa; Yuusaku Yokoyama
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-9-15
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Sep 
Date Detail:
Created Date:  2011-9-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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