Carbodiimide and Isocyanate Hydroboration by a Cyclic Carbodiphosphorane Catalyst

Authors

Ben A. Janda, Chapman UniversityFollow
Julie A. Tran, Chapman University
Daniel K. Chang, Chapman University
Gabriela C. Nerhood, Chapman University
O. Maduka Ogba, Chapman UniversityFollow
Allegra L. Liberman-Martin, Chapman UniversityFollow

Document Type

Article

Publication Date

10-17-2023

Abstract

We report hydroboration of carbodiimide and isocyanate substrates catalyzed by a cyclic carbodiphosphorane catalyst. The cyclic carbodiphosphorane outperformed the other Lewis basic carbon species tested, including other zerovalent carbon compounds, phosphorus ylides, an N-heterocyclic carbene, and an N-heterocyclic olefin. Hydroborations of seven carbodiimides and nine isocyanates were performed at room temperature to form N-boryl formamidine and N-boryl formamide products. Intermolecular competition experiments demonstrated the selective hydroboration of alkyl isocyanates over carbodiimide and ketone substrates. DFT calculations support a proposed mechanism involving activation of pinacolborane by the carbodiphosphorane catalyst, followed by hydride transfer and B−N bond formation.

Comments

This article was originally published in Chemistry: A European Journal in 2023. https://doi.org/10.1002/chem.202303095

Recommended Citation

B. A. Janda, J. A. Tran, D. K. Chang, G. C. Nerhood, O. Maduka Ogba, A. L. Liberman-Martin, Chem. Eur. J. 2023, e202303095. https://doi.org/10.1002/chem.202303095

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The authors

Creative Commons License

This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.