Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 49, Pages 12535-12539Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101617
Keywords
amination; melt; NaBHT; PEPPSI; solvent-free
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Funding
- NSERC (Canada) [CRDPJ 445703-12, RGPIN-2018-05584]
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NaBHT, paired with Pd-NHC catalysts, is effective in solvent-free cross-coupling amination. Its mild nucleophilicity and antioxidant properties make it more effective in handling functional group incompatibilities.
NaBHT (sodium 2,6-di-tert-butyl-4-methylphenolate), a strong, but hindered and lipophilic base, has been effectively paired with similarly lipophilic, high-reactivity Pd-NHC (N-heterocyclic carbene) catalysts to produce an ideal combination for performing solvent-free (melt) cross-coupling amination. The mild nucleophilicity of NaBHT, coupled with the anti-oxidant properties of its conjugate acid byproduct, BHT means the process seems to have no functional group incompatibilities. Highly effective coupling of base-sensitive and redox-active functional groups was observed in all cases with only 0.1-0.2 mol percent catalyst. Comparisons using the standard base for this reaction, KOtBu, led to poor couplings or complete degradation in most applications - only NaBHT works.
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