Formation of a C-C double bond from two aliphatic carbons. Multiple C-H activations in an iridium pincer complex
Författare
Summary, in English
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.
Avdelning/ar
Publiceringsår
2015
Språk
Engelska
Sidor
2060-2067
Publikation/Tidskrift/Serie
Chemical Science
Volym
6
Issue
3
Dokumenttyp
Artikel i tidskrift
Förlag
Royal Society of Chemistry
Ämne
- Chemical Sciences
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 2041-6539