Document Detail


Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.
MedLine Citation:
PMID:  22458307     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Friedel-Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S(2)O(8)(2-)) in the presence of the visible light catalyst, Ru(bpy)(3)Cl(2), at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron-rich arenes served as effective nucleophiles, forming new C-O or C-C bonds. In general, photocatalysis provided higher yields and better selectivities.
Authors:
Chunhui Dai; Francesco Meschini; Jagan M R Narayanam; Corey R J Stephenson
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2012-04-18
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  77     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 May 
Date Detail:
Created Date:  2012-05-04     Completed Date:  2012-09-28     Revised Date:  2013-12-06    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4425-31     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Catalysis
Light
Organometallic Compounds / chemistry*
Oxidation-Reduction
Photochemistry
Photolysis
Ruthenium / chemistry*
Temperature
Thermogravimetry
Grant Support
ID/Acronym/Agency:
R01 GM096129/GM/NIGMS NIH HHS; R01 GM096129-01/GM/NIGMS NIH HHS; R01-GM096129/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Organometallic Compounds; 7UI0TKC3U5/Ruthenium
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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