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Reductive Elimination of Hydrogen from Bis(trimethylsilyl)methyltin Trihydride and Mesityltin Trihydride
Author(s) -
Maudrich JakobJonathan,
Sindlinger Christian Patrick,
Aicher Frederik Sebastian William,
Eichele Klaus,
Schubert Hartmut,
Wesemann Lars
Publication year - 2017
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.201605317
Subject(s) - chemistry , carbene , reductive elimination , tin , adduct , hydride , elimination reaction , medicinal chemistry , trimethylsilyl , dehydrogenation , stoichiometry , hydrogen , organic chemistry , catalysis
Abstract Alkyltin trihydride [(Me 3 Si) 2 CHSnH 3 ] was synthesized and the reductive elimination of hydrogen from this species was investigated. A methyl‐substituted N‐heterocyclic carbene reacts with the organotrihydride in dependence on stoichiometry and solvent to give a series of products of the reductive elimination and dehydrogenative tin–tin bond formation. Besides characterization of the carbene adduct of the alkyltin(II) hydride, a Sn 4 chain was also isolated, encompassing two stannyl–stannylene sites, which are stabilized each as NHC‐adducts. Complete dehydrogenation resulted to give either a carbene‐stabilized distannyne or a metalloid Sn 9 ‐cluster salt. Reductive elimination of hydrogen was also achieved with an excess of diethylmethylamine to give the alkyltin(II) hydride as a Lewis base free tetramer [(RSnH) 4 ]. The method of cluster formation at low temperatures by hydrogen elimination was also transferred to the mesityl‐substituted tin trihydride MesSnH 3 . In this case [(MesSn) 10 ], showing a [5]prismane structure, was isolated in good yield and characterized. NMR spectroscopic features of the propellane‐type cluster [Trip 6 Sn 6 ] are reported.