The Phosphinoboration Reaction |
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| Authors: | Erika N. Daley Christopher M. Vogels Dr. Stephen J. Geier Dr. Andreas Decken Dr. Simon Doherty Prof. Dr. Stephen A. Westcott |
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| Affiliation: | 1. Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/;2. Department of Chemistry, University of New Brunswick, Frederiction, New Brunswick, E3B 5A3 (Canada);3. NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England) |
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| Abstract: | The synthesis of phosphinoboronate esters containing a single P? B bond is reported, together with preliminary reactivity studies towards a range of organic substrates. These compounds add readily to aldehydes, ketones, aldimines, and α,β‐unsaturated enones to give primarily the corresponding 1,2‐addition products containing a new P? C bond. The first examples of transition‐metal‐catalyzed phosphinoborations of C‐C multiple bonds in which P? C and B? C bonds are formed in a single step are also disclosed; allenes react by a highly regioselective 1,2‐addition whereas terminal alkynes undergo a formal 1,1‐addition. |
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| Keywords: | addition boron catalysis phosphines phosphinoboration |
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