Organic Letters
Organic Letters
5 years ago

N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters

N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
Dennis P. Curran, Takuji Kawamoto, Sean Gardner, Steven J. Geib, Thomas H. Allen
Boron–hydrogen bond insertion reactions of N-heterocyclic carbene (NHC) boranes and diazoesters can be catalyzed by NHC-boryl iodides and produce stable α-NHC-boryl esters. The conditions of the reaction resemble the previous rhodium-catalyzed transformations (only the catalyst is different); however, the mechanisms of the two reactions are probably very different. The new boryl iodide catalyzed method is adept at producing α-substituted-α-NHC-boryl esters, and this has led to a family of NHC-boryl esters with amino acid and amino-acid-like side chains.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01777

DOI: 10.1021/acs.orglett.7b01777

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