The Phosphinoboration Reaction†
Erika N. Daley
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorChristopher M. Vogels
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorDr. Stephen J. Geier
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorDr. Andreas Decken
Department of Chemistry, University of New Brunswick, Frederiction, New Brunswick, E3B 5A3 (Canada)
Search for more papers by this authorCorresponding Author
Dr. Simon Doherty
NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England)
Simon Doherty, NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England)
Stephen A. Westcott, Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorCorresponding Author
Prof. Dr. Stephen A. Westcott
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Simon Doherty, NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England)
Stephen A. Westcott, Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorErika N. Daley
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorChristopher M. Vogels
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorDr. Stephen J. Geier
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorDr. Andreas Decken
Department of Chemistry, University of New Brunswick, Frederiction, New Brunswick, E3B 5A3 (Canada)
Search for more papers by this authorCorresponding Author
Dr. Simon Doherty
NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England)
Simon Doherty, NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England)
Stephen A. Westcott, Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorCorresponding Author
Prof. Dr. Stephen A. Westcott
Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Simon Doherty, NUCAT, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (England)
Stephen A. Westcott, Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/
Search for more papers by this authorThis work was supported by the Natural Sciences and Engineering Research Council of Canada, Mount Allison University, the University of New Brunswick, and Newcastle University. Dan Durant is acknowledged for technical assistance. We would like to acknowledge the EPSRC UK National Service for Computational Chemistry Software (NSCCS) at Imperial College London for support of this work. We thank Dr. Keith J. Izod for his advice and support with DFT calculations and NBO analysis and anonymous reviewers for helpful comments.
Abstract
The synthesis of phosphinoboronate esters containing a single PB 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 PC bond. The first examples of transition-metal-catalyzed phosphinoborations of C-C multiple bonds in which PC and BC 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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