Reaction of B2(o-tol)4 with CO and Isocyanides: Cleavage of the C≡O Triple Bond and Direct C−H Borylations
Yuhei Katsuma
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan
Search for more papers by this authorNana Tsukahara
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan
Search for more papers by this authorLinlin Wu
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenyang Lin
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Makoto Yamashita
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603 Aichi Japan
Search for more papers by this authorYuhei Katsuma
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan
Search for more papers by this authorNana Tsukahara
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan
Search for more papers by this authorLinlin Wu
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenyang Lin
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Makoto Yamashita
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603 Aichi Japan
Search for more papers by this authorGraphical Abstract
Borane and CO: The reaction between highly Lewis acidic (o-tol)2B−B(o-tol)2 and CO afforded a mixture of boraindane and boroxine by complete cleavage of the C≡O triple bond. 13C labeling experiments demonstrated that the carbon atom in boraindane stems from CO. The reaction of diborane(4) with tBu−NC afforded an azaallene, while the reaction with Xyl−NC afforded cyclic compounds by direct C−H borylations.
Abstract
The reaction of highly Lewis acidic tetra(o-tolyl)diborane(4) with CO afforded a mixture of boraindane and boroxine by the cleavage of the C≡O triple bond. 13C labeling experiments confirmed that the carbon atom in the boraindane stems from CO. Simultaneously, formation of boroxine 3 could be considered as borylene transfer to capture the oxygen atom from CO. The reaction of diborane(4) with tBu−NC afforded an azaallene, while the reaction with Xyl−NC furnished cyclic compounds by direct C−H borylations.
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