Selective alpha-Monomethylation by an Amine-Borane/N,N-Dimethylformamide System as the Methyl Source
Selective alpha-Monomethylation by an Amine-Borane/N,N-Dimethylformamide System as the Methyl Source
复制标题
以胺-硼烷/N,N-二甲基甲酰胺系统作为甲基源进行选择性 α-单甲基化
DOI：
10.1002/anie.201804794
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发表时间：
2018
期刊：
影响因子：
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通讯作者：
Wang Yi-Feng
中科院分区：
文献类型：
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作者：
Xia Hui-Min;Zhang Feng-Lian;Ye Tian;Wang Yi-Feng
A new and practical α‐monomethylation strategy using an amine‐borane/N,N‐dimethylformamide (R3N‐BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α‐monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N‐BH3donated the remaining two hydrogen atoms. Such a unique reaction pathway enabled controllable assemblies of CDH2‐, CD2H‐, and CD3‐ units using Me2NH‐BH3/d7‐DMF, Me3N‐BD3/DMF and Me3N‐BD3/d7‐DMF systems, respectively. Further application of this method to the facile synthesis of anti‐inflammatory flurbiprofen and its varied deuterium‐labeled derivatives was demonstrated.
