Reaction of Bicyclic Zirconacyclopentenes with Aldehydes and a Potential Pathway to Condensed 5-7-6(Ar) Ring Systems

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Reaction of Bicyclic Zirconacyclopentenes with Aldehydes and a Potential Pathway to Condensed 5-7-6(Ar) Ring Systems

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Reaction of Bicyclic Zirconacyclopentenes with Aldehydes and a Potential Pathway to Condensed 5-7-6(Ar) Ring Systems

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA13-15915S" target="_blank" >GA13-15915S: Vývoj metod pro syntézu seskviterpenů založených na zirconocenové chemii</a><br>

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Svazek periodika

neuveden

Číslo periodika v rámci svazku

13

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

2868-2878

Kód UT WoS článku

000354213400011

EID výsledku v databázi Scopus

2-s2.0-84925237827