Synthetic Studies for the 1,3-Iterative Organoiron Approach to the Synthesis of Siculinine: Efficient Arylation Using a Diarylcuprate Reagent

Autor:	Sarah Thomas, G. Richard Stephenson, Michael Tinkl, Ian M. Palotai
Rok vydání:	2013
Předmět:	Hydride Organic Chemistry Regioselectivity chemistry.chemical_element Copper Combinatorial chemistry Hydrolysis chemistry.chemical_compound chemistry Yield (chemistry) Reagent Organic chemistry Chelation Dimethyl sulfide Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2013:1895-1901
ISSN:	1434-193X
DOI:	10.1002/ejoc.201201056
Popis:	Disubstituted (cyclohexadienyl)iron(1+) complex 2b is prepared by an improved route that starts from 1,2-dimethoxycyclohexa-1,4-diene 3. In five steps, the synthesis of 2b is achieved by complexation with Fe(CO)5, hydride abstraction, hydrolysis, addition of EtO2CCH2ZrBr, and reaction with HBF4. In the presence of dimethyl sulfide, the reaction of 2b with 2-[CH2N(CH2CH=CH2)2]-functionalized diarylcuprate reagent 7 gave the 5α-arylcyclohexadiene complex 1b in 88% yield. A DFT study compared diarylzinc and diarylcuprate reagents containing chelating CH2NMe2 substituents.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e37cac1165b78adfc5b48511bcd314ba https://doi.org/10.1002/ejoc.201201056 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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