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Convenient Cyclopentadiene Modifications for Building Versatile (Radio‐)Metal Cyclopentadienyl Frameworks
Author(s) -
Lengacher Raphael,
Braband Henrik,
Csucker Joshua,
Alberto Roger
Publication year - 2021
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202100163
Subject(s) - chemistry , bifunctional , cyclopentadiene , linker , alkyne , azide , click chemistry , nucleophilic substitution , metalation , cyclopentadienyl complex , chloride , block (permutation group theory) , phenylacetylene , chlorosilane , yield (engineering) , combinatorial chemistry , nucleophile , organic chemistry , geometry , mathematics , computer science , catalysis , operating system , materials science , silicon , metallurgy
The synthesis of a bifunctional cyclopentadiene‐based building block, bearing an alkyl linker with a terminal chloride and an ester group is described. This building block was modified by nucleophilic substitution, leading to two new fac ‐[Re(CO) 3 ] + containing derivatives of known drug candidates for brain imaging and multi‐drug resistance in cancer in as few as two steps. Furthermore, the chloride was replaced by an azide, which was subsequently coupled to phenylacetylene as a model alkyne to demonstrate its versatility for undergoing Click‐type reactions. The resulting triazole was labelled with 99m Tc to yield the corresponding piano‐stool complex in a radiochemical purity of 86 %. The identities were confirmed by coinjection with the Re homologue.