Reaction of Bicyclic Zirconacyclopentenes with Aldehydes and a Potential Pathway to Condensed 5-7-6(Ar) Ring Systems
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10296150" target="_blank" >RIV/00216208:11310/15:10296150 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201500248" target="_blank" >http://dx.doi.org/10.1002/ejoc.201500248</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201500248" target="_blank" >10.1002/ejoc.201500248</a>
Alternative languages
Result language
angličtina
Original language name
Reaction of Bicyclic Zirconacyclopentenes with Aldehydes and a Potential Pathway to Condensed 5-7-6(Ar) Ring Systems
Original language description
Bicyclic zirconacyclopentenes prepared by the reactions of 1,6- and 1,7-enynes with [Cp2ZrBu2] (Negishi reagent) reacted with a plethora of aldehydes (aryl, heteroaryl, alkyl, alpha,beta-unsaturated) by chemo-and stereoselective insertion into the sp(3)C-Zr bond to give the corresponding oxazirconacycloheptenes. Subsequent hydrolysis or halogenolysis provided the corresponding alcohols 4 (31-74% isolated yields) or halides 10 (35-50% isolated yields). The oxazirconacycloheptenes prepared by the insertion of 2-iodobenzaldehyde were also subjected to intramolecular coupling in the presence of CuCl and additives, and compounds possessing the condensed 5-7-6(aryl) ring system were obtained in reasonable isolated yields (32-46%). The same ring system was also prepared by the Pd-catalyzed coupling of dihalo derivatives 10 (38-42% H-1 NMR yields). Moreover, the mechanism of the unproductive side-reaction leading to ketones during the reaction with CuCl was elucidated.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA13-15915S" target="_blank" >GA13-15915S: Development of zirconocene-based methods for sesquiterpenoids synthesis</a><br>
Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
neuveden
Issue of the periodical within the volume
13
Country of publishing house
DE - GERMANY
Number of pages
11
Pages from-to
2868-2878
UT code for WoS article
000354213400011
EID of the result in the Scopus database
2-s2.0-84925237827