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Introduction of terminal alkynes into the 2-and 8-positions of the Troger's base core via Sonogashira reaction of 2,8-diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

In English

Författare

Summary, in English

Conditions for the introduction of terminal alkynes into the 2- and 8-positions of the Troger's base core via Sonogashira reaction of 2,8-diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine were established. Only the use of the bulky and electron-rich phosphine P(t-Bu)(3) as a ligand for the palladium catalyst allowed for the Sonogashira reaction to proceed effectively. In addition, excessive equivalents of the alkyne were found to increase the yields of the coupling. The established optimal conditions for the introduction of terminal alkynes into the Troger's base core were applied to differently aryl- and pyridyl-substituted terminal alkynes to afford new analogues of Troger's base 3a-g in moderate to excellent yields.

Publiceringsår

2002

Språk

Engelska

Sidor

2761-2765

Publikation/Tidskrift/Serie

Synthesis

Issue

18

Dokumenttyp

Artikel i tidskrift

Förlag

Oxford Polytechnic, Oxford

Ämne

  • Organic Chemistry

Nyckelord

  • ligands
  • alkynes
  • Troger's base
  • Sonogashira reaction
  • supramolecular
  • chemistry

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 0039-7881