Regioselective allylic alkylation and etherification catalyzed by in situ generated N-heterocyclic carbene ruthenium complexes

Gurbuz N., Ozdemir I., CETINKAYA B., RENAUD J., DEMERSEMAN B., BRUNEAU C.

TETRAHEDRON LETTERS, cilt.47, sa.4, ss.535-538, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 47 Sayı: 4
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1016/j.tetlet.2005.11.051
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.535-538
  • İnönü Üniversitesi Adresli: Evet

Özet

Benzimidazolium halides are used for the first time as ligand precursors in ruthenium-catalyzed substitution of allylic carbonates and chlorides by carbon nucleophiles and phenols, respectively. After generation of diaminocarbene species upon deprotonation by tBuOK, their association with [Cp*Ru(MeCN)(3)]PF6 induces a very high regioselectivity in favor of the branched isomers when cinnamyl derivatives are used as starting substrates. They also provide good regioselectivities for the allylation of phenols by unsymmetrical aliphatic allylic substrates such as 3-chloro-4-phenylbut-1-ene, and thus provide a straightforward access to new allylic phenyl ethers. (c) 2005 Elsevier Ltd. All rights reserved.