A novel ditopic ring-expanded N-heterocyclic carbene ligand-assisted Suzuki-Miyaura coupling reaction in aqueous media

KARACA E. Ö., AKKOÇ M., TAHIR M. N., ARICI C., IMIK F., GÜRBÜZ N., ...Daha Fazla

TETRAHEDRON LETTERS, cilt.58, sa.36, ss.3529-3532, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 36
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tetlet.2017.07.096
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3529-3532
  • Anahtar Kelimeler: Ditopic ring-expanded N-heterocyclic carbene, Suzuki-Miyaura coupling, C-C bond formation, Palladium, TRANSITION-METAL-COMPLEXES, ROOM-TEMPERATURE, ARYL CHLORIDES, PALLADIUM(II) COMPLEX, ARYLBORONIC ACIDS, WATER, CATALYSTS, NHC, HECK, ELECTROPHILES
  • İnönü Üniversitesi Adresli: Evet

Özet

A series of seven-membered ditopic ring-expanded N-heterocyclic carbene (dre-NHC) precursors, bearing sterically demanding and electron-rich aryl groups, were synthesised in moderate yields via the reaction of 1,2,4,5-tetrakis(bromomethyl)benzene with the corresponding N,N'-diarylformamidines in the presence of K2CO3 in acetonitrile under an air atmosphere. All new compounds were characterised by HRMS, NMR spectroscopy, and microanalysis, as well as X-ray crystallography for compound lc. The development of an efficient catalytic system for the Suzuki-Miyaura coupling reaction of aryl chlorides with various boronic acids was also investigated using the in situ generated dre-NHC ligands. (C) 2017 Elsevier Ltd. All rights reserved.