Introduction of Terminal Alkynes into the 2- and 8-Positions of the Tröger’s Base Core via Sonogashira Reaction of 2,8-Diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

Jacob Jensen; Michal Strozyk; Kenneth Wärnmark

doi:10.1055/s-2002-35989

PAPER

Introduction of Terminal Alkynes into the 2- and 8-Positions of the Tröger’s Base Core via Sonogashira Reaction of 2,8-Diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

Jacob Jensen, Michal Strozyk, Kenneth Wärnmark*
Organic Chemistry 1, Department of Chemistry, Lund University, P.O. Box 124, 221 00 Lund, Sweden
Fax: +46(46)2224119; e-Mail: Kenneth.Warnmark@orgk1.lu.se;

Abstract

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Abstract

Conditions for the introduction of terminal alkynes into the 2- and 8-positions of the Tröger’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 Tröger’s base core were applied to differently aryl- and pyridyl-substituted terminal alkynes to afford new analogues of Tröger’s base 3a-g in moderate to excellent yields.

Key words

Tröger’s base - Sonogashira reaction - alkynes - ligands - supramolecular chemistry

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Referenzen

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