Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 7, Pages 2121-2125Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410033
Keywords
addition; boron; catalysis; phosphines; phosphinoboration
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Funding
- Natural Sciences and Engineering Research Council of Canada
- Mount Allison University
- University of New Brunswick
- Newcastle University
- EPSRC UK National Service for Computational Chemistry Software (NSCCS) at Imperial College London
- EPSRC [EP/J003921/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/J003921/1] Funding Source: researchfish
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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 alpha,beta-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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