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Formation of a C-C double bond from two aliphatic carbons. Multiple C-H activations in an iridium pincer complex
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1553-4027
2015 (English)In: Chemical Science, ISSN 2041-6520, Vol. 6, no 3, 2060-2067 p.Article in journal (Refereed) Published
Abstract [en]

The search for novel, atom-economic methods for the formation of C-C bonds is of crucial importance in synthetic chemistry. Especially attractive are reactions where C-C bonds are formed through C-H activation, but the coupling of unactivated, alkane-type C-sp3-H bonds remains an unsolved challenge. Here, we report iridium-mediated intramolecular coupling reactions involving up to four unactivated C-sp3-H bonds to give carbon-carbon double bonds under the extrusion of dihydrogen. The reaction described herein is completely reversible and the direction can be controlled by altering the reaction conditions. With a hydrogen acceptor present a C-C double bond is formed, while reacting under dihydrogen pressure leads to the reverse process, with some of the steps representing net C-sp3-C-sp3 bond cleavage. Mechanistic investigations revealed a conceptually-novel overall reactivity pattern where insertion or deinsertion of an Ir carbene moiety, formed via double C-H activation, into an Ir-C bond is responsible for the key C-C bond formation and cleavage steps.

Place, publisher, year, edition, pages
2015. Vol. 6, no 3, 2060-2067 p.
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-161629DOI: 10.1039/c4sc03839hISI: 000349832600060ScopusID: 2-s2.0-84923167393OAI: diva2:797641

QC 20150324

Available from: 2015-03-24 Created: 2015-03-13 Last updated: 2015-03-24Bibliographically approved

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