233667-59-9Relevant academic research and scientific papers
A convenient short cut from aromatic iodides to alkynylstannanes and their use for the straightforward preparation of polyacetylene and polymetallaacetylene polymers
Antonelli, Eleonora,Rosi, Patrizia,Lo Sterzo, Claudio,Viola, Egidio
, p. 210 - 222 (1999)
The palladium-catalyzed cross-coupling reaction (Stille coupling) of aromatic iodides Ar-I and tributyl(ethynyl)tin Bu3SnC≡CH form the aromatic acetylides Ar-C≡CH and the side product tributyltin iodide Bu3SnI in equimolar amount. In situ addition of lithium diisopropylamide (LDA) to this crude mixture directly affords the tributyl(ethynyl)tin aromatics Ar-C≡C-SnBu3 in high yield. In the case of the bis(iodoaromatic) I-Ar-I (Ar = phenyl, thiophene), this straightforward transformation affords the corresponding bis[tributyl(ethynyl)tin]derivative Bu3Sn-C≡C-Ar-C≡C-SnBu3. In the presence of Pd this latter species can be directly reacted with a second bis(iodoaromatic) or a bis(metaliodide) unit to form acetylenic and metallaacetylenic polymers with tailored monomer units inserted in a stereoregular polymer chain.
