Abstract
Stable bis(gold(I) alkynyl) complexes of tetraethynylethene (TEE) derivatives were readily prepared and employed in Sonogashira-like palladium-catalyzed phosphine-gold(I) halide elimination reactions with aryl iodides and redox-active tetrathiafulvalene (TTF) mono- and bisiodides. This presents a particularly convenient method for the preparation of symmetrical and asymmetrical tetrathiafulvalene (TTF)-fused radiaannulenes in good yields.
Highlights
M etal-catalyzed coupling reactions of terminal alkynes have allowed the preparation of a large variety of carbonrich materials, such as π-conjugated oligomers and macrocyclic structures with interesting optical and redox properties.[1]
Gold(I) alkynyl complexes were shown by Bruce, Low, and coworkers4e,f,6 to undergo Pd-catalyzed gold(I)−phosphine halide elimination reactions with 1-iodoalkynes and aryl iodides, which can be performed under base-free conditions
This has allowed the synthesis of metal-capped oligoynes with as many as 19 or 24 carbons between the metal centers.4f It should be noted that phospine−gold(I) alkynyl complexes, being more stable than copper(I) and silver(I) alkynyl complexes, have themselves found wide interest in supramolecular and materials science, in particular owing to their luminescent properties.[7]
Summary
M etal-catalyzed coupling reactions of terminal alkynes have allowed the preparation of a large variety of carbonrich materials, such as π-conjugated oligomers and macrocyclic structures with interesting optical and redox properties.[1]. The bulky triphenylphosphine-gold(I) (AuPPh3) fragment presents another convenient stabilizing end group for terminal alkynes.[4] Bruce et al.4d−g have shown that phosphine−gold(I) complexes of 1,3-butadiyne and oligoynes can be readily prepared and isolated (Figure 1).
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