Document Detail


Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.
MedLine Citation:
PMID:  23035947     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Described is a Cu-catalyzed directed carbozincation of cyclopropenes with organozinc reagents prepared by I/Mg/Zn exchange. This protocol broadens the scope with respect to functional group tolerance and enables use of aryl iodide precursors, rather than purified diorganozinc precursors. Critical to diastereoselectivity of the carbozincation step is the removal of magnesium halide salts after transmetalation with ZnCl(2).
Authors:
Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2012-10-19
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  77     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-02     Completed Date:  2013-03-17     Revised Date:  2013-11-06    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9900-4     Citation Subset:  IM    
Affiliation:
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware, 19716, United States.
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Copper / chemistry*
Cyclopropanes / chemistry*
Indicators and Reagents
Iodides / chemistry*
Magnesium / chemistry*
Molecular Structure
Zinc / chemistry*
Grant Support
ID/Acronym/Agency:
R01 GM068640/GM/NIGMS NIH HHS; R01 GM068650/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Cyclopropanes; 0/Indicators and Reagents; 0/Iodides; 7439-95-4/Magnesium; 7440-50-8/Copper; 7440-66-6/Zinc
Comments/Corrections

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