Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent.

Chem Commun (Camb)

WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.

Published: March 2015

1-Lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-)butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media. A Me6TREN stabilized monomer of the t-butyl complex represents the first 1,2-dihydropyridyllithium complex to be characterized crystallographically.

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http://dx.doi.org/10.1039/c4cc06421fDOI Listing

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