Dual Functionalization of α-Monoboryl Carbanions through Deoxygenative Enolization with Carboxylic Acids
Wei Sun
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorDr. Lu Wang
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Chungu Xia
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Chao Liu
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
Search for more papers by this authorWei Sun
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorDr. Lu Wang
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Chungu Xia
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Chao Liu
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000 P. R. China
Search for more papers by this authorDedicated to Professor Xiyan Lu on the occasion of his 90th birthday
Abstract
A dual functionalization of 1,1-diborylalkanes through deoxygenative enolization with carboxylic acids was developed. 1,1-Diborylalkanes were activated by MeLi to generate α-monoboryl carbanions. In situ IR spectroscopy indicated an interaction between carboxylic acid and 1,1-diborylalkane before addition of the activation reagent. Release of the active α-monoboryl carbanion from the masked form was necessary for its reaction with carboxylate to afford enolate species. Electrophilic trapping of enolate species with various electrophiles achieved dual functionalization of 1,1-diborylalkanes to afford a variety of α-mono, di-, and tri-substituted ketones.
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