双生的
化学
碳负离子
结合
脱质子化
硼
组合化学
等价物
有机化学
药物化学
立体化学
离子
生物化学
数学分析
数学
作者
Lucia Wang,Sheng‐Jia Lin,Emmanuel Santos,Jenna Pralat,Kaylyn Spotton,Abhishek Sharma
标识
DOI:10.1021/acs.joc.2c00914
摘要
Conjugate addition of α-boron-stabilized carbanions is an underexplored reaction modality. Existing methods require deborylation of geminal di-/triboryl alkanes and/or the presence of additional activating groups. We report the 1,4-addition of α,α-diboryl carbanions generated via deprotonation of the corresponding geminal diborons. The methodology provided a general route to highly substituted and synthetically useful γ,γ-diboryl ketones. The development of geminal diborons as soft pronucleophiles also enabled their use as acyl anion equivalents via a one-pot tandem conjugate addition–oxidation sequence.
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