Synthesis of 2,8-Disubstituted Analogues of Troeger’s Base

Abstract

Starting from the 2,8-dibromo- and the 2,8-diiodo-substituted Troeger’s base analogues 1 and 2, several new symmetrically disubstituted derivatives 4, 5, and 7-17 could be obtained by transition metal-catalyzed cross-coupling reactions or other functionalizations like borylation or protecting group operations. For the first time, conditions for a highly efficient Suzuki cross-coupling reaction involving the Troeger’s base core were established.

Key words

Troeger’s base - cross-coupling reactions - Suzuki reaction

References

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  To be exact the name should be spelled ‘Tröger’s base’ (Ref. [1] ). However, we used the commonly used ‘international’ spelling ‘Troeger’ throughout this paper in order to avoid misunderstandings.

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