Document Detail


A versatile synthesis of functionalized pentahelicenes.
MedLine Citation:
PMID:  20863066     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A general synthetic methodology for the preparation of functionalized (hetero)helicenes has been developed. It employs the sequence of a double propargyl organometallics (Li, Mg, Ga/In) addition to a tolan-2,2'-dialdehyde-type intermediate, a cobalt-catalyzed/cobalt-mediated [2 + 2 + 2] cycloisomerization of a triyne intermediate, and a double silica gel-assisted acetic acid elimination to receive pentahelicene, 1,14-diazapentahelicene, and 3,12-dichloro-, 3,12-dichloro-7-trimethylsilyl-, and 3,12-di-tert-butylpentahelicene. 3,12-Dichloropentahelicene undergoes a Suzuki-Miyaura coupling with aryl boronic acids (or ester) under palladium catalysis to afford 3,12-diarylpentahelicenes.
Authors:
Olivier Songis; Jirí Mísek; Markus B Schmid; Adrian Kollárovic; Irena G Stará; David Saman; Ivana Císarová; Ivo Starý
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-10-08     Completed Date:  2011-01-25     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6889-99     Citation Subset:  IM    
Affiliation:
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
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MeSH Terms
Descriptor/Qualifier:
Alkynes / chemistry*
Catalysis
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Structure
Organometallic Compounds / chemistry
Polycyclic Compounds / chemical synthesis*,  chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
0/Alkynes; 0/Organometallic Compounds; 0/Polycyclic Compounds; 0/helicenes

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