Abstract
E,E,E)-1,6,11-Tris(arenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,11-trienes, 1, are prepared from arenesulfonamides and trans-1,4-dibromo-2-butene. Macrocycles 1 coordinate palladium(0), platinum(0), and silver(I), and the palladium complexes are useful and reutilizable catalysts or precatalysts in Suzuki cross-couplings, butadiene telomerizations, hydroarylation of alkynes, and in the Heck reaction. Structurally related macrocycles are also available by similar synthetic procedures.
Highlights
Nitrogen-containing 15-membered macrocycles with endocyclic olefins are uncommon.[1]
We discovered macrocycles 1 in a serendipitous manner when exploring the palladiumcatalyzed reaction of arenesulfonamides with 2-butene-1,4-diol biscarbonate (Scheme 1).4 10, 15, and 20-membered cycles were isolated and identified
We have reported three different synthetic pathways "a", "b", and "c" for the synthesis of the triazatriolefinic macrocycles 1 based on three different disconnecting approaches for the final condensation step (Figure 3).[7]
Summary
Nitrogen-containing 15-membered macrocycles with endocyclic olefins are uncommon.[1] A few nitrogen-containing monoolefinic 15-membered rings have been prepared by metathesis.[2]. Macrocycles 1 (Figure 1) are structurally related to the 12-membered carbocyclic cyclododeca-1,5,9-trienes, 2. The nickel complexes of 2 have played a fundamental role in catalysis and in organonickel chemistry.[3]. We discovered macrocycles 1 in a serendipitous manner when exploring the palladiumcatalyzed reaction of arenesulfonamides with 2-butene-1,4-diol biscarbonate (Scheme 1).4 10-, 15-, and 20-membered cycles were isolated and identified. One part of the 15-membered rings appeared in the form of their palladium(0) complexes 4 (vide infra). Since preparation of 1 involves the use of trans-1,4-dibromo-2-butene, different structurally related macrocycles can be built up by working with, for example, cis-1,4-dibromo-2-butene or 1,2bis(bromomethyl)benzene
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