Efficient Modular Synthesis of Isomeric Mono- and Bispyridyl[2.2]paracyclophanes by Palladium-Catalyzed Cross- Coupling Reactions

Braun C., Spulıng E., Heıne N. B., Çakıcı M., Nieger M., Braese S.

ADVANCED SYNTHESIS & CATALYSIS, vol.358, no.10, pp.1664-1670, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 358 Issue: 10
  • Publication Date: 2016
  • Doi Number: 10.1002/adsc.201600066
  • Journal Name: ADVANCED SYNTHESIS & CATALYSIS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1664-1670
  • Keywords: biaryls, Kumada coupling, [2.2]paracyclophanes, stannylation, Stille coupling, Suzuki coupling, SPACE CONJUGATED POLYMERS, THROUGH-SPACE, ELECTROPHILIC SUBSTITUTION, POLYQUINOLINE PREPOLYMERS, BIDENTATE LIGANDS, FACILE SYNTHESIS, BUILDING-BLOCKS, MACRO RINGS, PLANAR, PALLADACYCLE
  • Ataturk University Affiliated: Yes

Abstract

Pyridyl-substituted [2.2]paracyclophanes build a multifunctional structural motif that is useful in material chemistry, catalysis and for luminescent structures. Nonetheless, there is still a lack of general methods for the synthesis of these structures tolerating easily accessible bromides as well as different isomeric pyridyl groups. Hence the coupling of functionalized [2.2]paracyclophanes with various substituted and functionalized pyridyl derivatives was achieved using Stille, Suzuki and Kumada coupling conditions. Hereby the Stille coupling of a [2.2]paracyclophane is presented as a versatile reaction for the formation of heteromeric [2.2]paracyclophane-containing biaryl structures.