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A Tetrakis(tetrazolyl) Analogue of EDTA
Author(s) -
Touti Faycal,
Maurin Philippe,
Hasserodt Jens
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900016
Subject(s) - synthon , chemistry , moiety , tetrazole , denticity , yield (engineering) , ligand (biochemistry) , combinatorial chemistry , coordination complex , protecting group , catalysis , stereochemistry , metal , organic chemistry , biochemistry , materials science , receptor , alkyl , metallurgy
The tetrazole moiety is usually established in situ with the corresponding inconveniences, such as reactant incompatibility, yield. In most of these cases, the tetrazole is formed in its nonprotected form. Subsequent protection is unattractive because of the promiscuous formation of two regioisomers. No particular protecting group has seen widespread use. The growing field of site‐selective oxidation of unactivated hydrocarbons makes use of metal complexes based on multidentate ligands displaying nitrogen coordination sites. We have characterized an easily accessible, benzyl‐protected synthon that allows the convergent introduction of the tetrazolylmethyl moiety and its smooth deprotection by catalytic hydrogenation. With the straightforward synthesis of the new hexadentate ligand EDTT, we have demonstrated the utility of this synthon for the fields of coordination, medicinal, and organocatalytic chemistry. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)