N-Heterocyclic Carbene Boranes are Good Hydride Donors

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• 作者：Markus Horn ; Herbert Mayr ; Emmanuel Lac么te ; Everett Merling ; Jordan Deaner ; Sarah Wells ; Timothy McFadden ; Dennis P. Curran
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：January 6, 2012
• 年：2012
• 卷：14
• 期：1
• 页码：82-85
• 全文大小：718K
• 年卷期：v.14,no.1(January 6, 2012)
• ISSN：1523-7052

文摘

The nucleophilicity parameters (N) of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene borane and 1,3-dimethylimidazol-2-ylidene borane are 9.55 and 11.88. This places N-heterocyclic carbene boranes (NHC-boranes) among the most nucleophilic classes of neutral hydride donors. Reductions of highly electron-poor C鈺怤 and C鈺怌 bonds provide hydrogenation products along with new, stable borylated products. The results suggest that NHC-boranes have considerable untapped potential as neutral organic reductants.