Premium
Synthesis of Long, Palladium End‐Capped Polyynes through the Use of Asymmetric 1‐Iodopolyynes
Author(s) -
Pigulski Bartłomiej,
Gulia Nurbey,
Szafert Sławomir
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502737
Subject(s) - palladium , chemistry , combinatorial chemistry , organic chemistry , catalysis
The synthesis of a unique series of long, asymmetric 1‐iodopolyynes ( 1 ‐C n I and 2 ‐C n I) with the sp‐hybridized carbon chain up to a decapentayne is reported. These compounds were then used as substrates in reactions with Pd(PPh 3 ) 4 leading to another series of palladium end‐capped polyynes, which were unstable in solution. Organometallic octatetraynes 1 ‐C 8 [Pd]I, 2 ‐C 8 [Pd]I, and decapentayne 1 ‐C 10 [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.