NaBH4 in N-methylpyrrolidone: A safe alternative for hydride displacement reaction

Enhanced reactivity of NaBH4 was observed as a solution in N-methylpyrrolidone (NMP). Thus, a simple protocol for debromination of alkyl bromide and sulfonate is devised with NMP as a key solvent. Also described is a new mixed borohydride system, NaBH4-LiOTf-NMP, which works as an alternative to NaB...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2001-10, Vol.11 (20), p.2787-2789
Main Authors: TORISAWA, Yasuhiro, NISHI, Takao, MINAMIKAWA, Jun-Ichi
Format: Article
Language:English
Subjects:
Borohydrides - chemistry
Bromine - chemistry
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Oxidation-Reduction
Preparations and properties
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
Pyrrolidinones - pharmacology
Teratogens - chemical synthesis
Teratogens - chemistry
Teratogens - pharmacology
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Summary:Enhanced reactivity of NaBH4 was observed as a solution in N-methylpyrrolidone (NMP). Thus, a simple protocol for debromination of alkyl bromide and sulfonate is devised with NMP as a key solvent. Also described is a new mixed borohydride system, NaBH4-LiOTf-NMP, which works as an alternative to NaBH3CN for the SN2 type displacement. No reports have ever revealed usefulness of NMP in borohydride reduction.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)00565-0