Affiliation:
1. Chemistry and Biochemistry Program Schmid College of Science and Technology Chapman University 450 North Center Street Orange CA 92866 USA
Abstract
AbstractWe 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.
Funder
American Chemical Society Petroleum Research Fund
Division of Chemistry
Chapman University
Arnold and Mabel Beckman Foundation
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
1 articles.
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