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An oxidative carbon–carbon bond-forming reaction proceeds via an isolable iminium ion

✍ Scribed by Tsang, Althea S.-K.; Jensen, Paul; Hook, James M.; Hashmi, A. Stephen K.; Todd, Matthew H.

Book ID
111980562
Publisher
International Union of Pure and Applied Chemistry
Year
2011
Tongue
English
Weight
470 KB
Volume
83
Category
Article
ISSN
0033-4545

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✦ Synopsis

The mechanism of our previously reported DDQ-mediated oxidative C–C bond-forming reaction is investigated. We are able to trap and characterize an iminium ion intermediate with X-ray crystallography, elemental analysis, and solid-state NMR spectroscopy; to our knowledge this is the first time this putative intermediate ion has been directly observed in such cross-dehydrogenative couplings (CDCs). The intermediate can be reacted with a range of nucleo-philes, including a malonate that is not amenable to a one-pot reaction protocol.

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