Synthetic studies for the 1,3-iterative organoiron approach to the synthesis of siculinine: efficient arylation using a diarylcuprate reagent

Stephenson, George ORCID: https://orcid.org/0000-0003-1487-9178, Palotai, Ian M., Thomas, Sarah and Tinkl, Michael (2013) Synthetic studies for the 1,3-iterative organoiron approach to the synthesis of siculinine: efficient arylation using a diarylcuprate reagent. European Journal of Organic Chemistry, 2013 (10). 1895–1901. ISSN 1434-193X

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Abstract

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.

Item Type:	Article
Uncontrolled Keywords:	synthesis design ,arylation,c–c coupling,alkaloids,regioselectivity,iron,copper,density functional calculations,chemistry(all) ,/dk/atira/pure/subjectarea/asjc/1600
Faculty \ School:	Faculty of Science > School of Chemistry
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Pure Connector
Date Deposited:	04 Jan 2017 00:02
Last Modified:	22 Oct 2022 02:03
URI:	https://ueaeprints.uea.ac.uk/id/eprint/61893
DOI:	10.1002/ejoc.201201056

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