Synthesis of Long, Palladium End-Capped Polyynes through the Use of Asymmetric 1-Iodopolyynes.
The synthesis of a unique series of long, asymmetric 1-iodopolyynes (1-Cn I and 2-Cn I) with the sp-hybridized carbon chain up to a decapentayne is reported. These compounds were then used as substrates in reactions with Pd(PPh3 )4 leading to another series of palladium end-capped polyynes, which were unstable in solution. Organometallic octatetraynes 1-C8 [Pd]I, 2-C8 [Pd]I, and decapentayne 1-C10 [Pd]I are palladium end-capped polyyne compounds with the longest carbon chains reported so far. All the complexes as well as their organic precursors were fully characterized by NMR, HRMS(ESI), IR, TGA-DTA, and UV/Vis techniques, and the X-ray crystal structures of two silyl-protected precursors and one palladium complex are presented. The synthetic approach for palladium species is envisioned as a general route for the synthesis of labile organometallic polyynes.
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław (Poland) http://www.zb1.chem.uni.wroc.pl.
Bartłomiej
B
Pigulski
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław (Poland) http://www.zb1.chem.uni.wroc.pl.
Nurbey
N
Gulia
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław (Poland) http://www.zb1.chem.uni.wroc.pl. slawomir.szafert@chem.uni.wroc.pl.
Sławomir
S
Szafert
alkynes; cross-coupling; hyperconjugation; iodine; palladium