硼烷
化学
硼氢化钠
硼烷
胺气处理
吡啶
溶剂
有机化学
四氢呋喃
硼
催化作用
作者
P. Veeraraghavan Ramachandran,Henry J. Hamann,Randy Lin,Aman Singh
标识
DOI:10.1021/acs.oprd.3c00031
摘要
In situ generated, transient sodium monohydroxyborohydride readily reacts with a present amine to form amine-borane adducts in ethyl acetate at room temperature. Synthesis of heteroaromatic pyridine-, 2-picoline-, and 5-ethyl-2-methylpyridine-boranes, those relevant to large-scale reductive aminations, has been demonstrated at 100 mmol scale, and pyridine-borane at 1.1 mole scale. This first report substituting ethyl acetate for tetrahydrofuran, the traditional solvent for amine-borane synthesis, allows for activation of sodium borohydride by the aqueous portion of the heterogeneous dual-solvent system. These factors make this green protocol more economical than those currently available for the large-scale production of amine-boranes as demonstrated, quantitatively, by the computed green chemistry metrics.
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