Intermolecular coupling of isomerizable alkenes to heterocycles via rhodium-catalyzed C-H bond activation.
This reports first intermolecular coupling of unactivated alkenes, including isomerizable alkenes, to a range of heterocycles using a Rh(I) catalyst. A variety of functional groups were incorporated, including esters, nitriles, and acetals. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions.
Tan
Kian L
KL
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Bergman
Robert G
RG
Ellman
Jonathan A
JA
D000475:Alkenes / Q000737:chemistry*; D001562:Benzimidazoles / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007536:Isomerism; D012238:Rhodium / Q000737:chemistry*
D000475:Alkenes; D001562:Benzimidazoles; D006571:Heterocyclic Compounds; C117224:1-hexene; D012238:Rhodium; C031000:benzimidazole