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Oxidative C-C Coupling Reactions of Benzofused Heterocycles Utilizing DDQ

Villafane, Louis (2014) Oxidative C-C Coupling Reactions of Benzofused Heterocycles Utilizing DDQ. Master's Thesis, University of Pittsburgh. (Unpublished)

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2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated oxidative coupling chemistry that was previously developed in the Floreancig group for coupling with chromene cations has been expanded to include other benzofused heterocycles, including benzoxathioles, and is described herin. The reactivity of these cationic intermediates was utilized to rapidly furnish coupled benzofused heterocycles. The reactivity of the cationic intermediates was explored via addition of a number of nucleophiles and the electronics of the substrate were altered to determine the scope of the substrate in this type of transformation. In addition a one-pot method was developed to access spiro compounds, in the orthoester oxidation state, containing a synthetic handle for further manipulation.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Villafane, Louislav17@pitt.eduLAV17
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberHorne, SethHorne@pitt.eduHORNE
Date: 4 February 2014
Date Type: Publication
Defense Date: 14 December 2013
Approval Date: 4 February 2014
Submission Date: 6 December 2013
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 68
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: Oxidation, Fragment Coupling, Heterocycles
Date Deposited: 04 Feb 2014 16:07
Last Modified: 15 Nov 2016 14:16


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