Versatile Synthesis of α-Oxygen Organoboron Compounds via Photo-Induced Siloxycarbene†
Xiongxiong Lu
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
The authors contributed equally to this work.
Search for more papers by this authorQingbin Zhao
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
The authors contributed equally to this work.
Search for more papers by this authorDehai Cao
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Search for more papers by this authorPan Xu
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Search for more papers by this authorXuenian Chen
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Henan Key Laboratory of Boron Chemistry and Advanced Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorCorresponding Author
Zhenxing Liu
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
E-mail: [email protected]Search for more papers by this authorXiongxiong Lu
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
The authors contributed equally to this work.
Search for more papers by this authorQingbin Zhao
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
The authors contributed equally to this work.
Search for more papers by this authorDehai Cao
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Search for more papers by this authorPan Xu
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Search for more papers by this authorXuenian Chen
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Henan Key Laboratory of Boron Chemistry and Advanced Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 China
Search for more papers by this authorCorresponding Author
Zhenxing Liu
College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
E-mail: [email protected]Search for more papers by this authorDedicated to the Special Issue of Boron Chemistry.
Comprehensive Summary
A novel method for synthesizing α-oxygen organoboron compounds has been developed through acylsilane-based carbene insertion reactions into C—B bonds. As coupling partners, readily available organoboron compounds (alkenyl, allyl, and allenyl B(pin)) were employed. Based on the substrates, pure insertion into C—B bonds or insertion followed by a siloxy group rearrangement process (from carbon to boron) would occur, delivering the α-oxygen organoboron compounds with great diversities. Control experiments demonstrated that the electronic effect of the substituents mainly controlled the rearrangement process. Besides, no matter which isomer of substrate (Z or E) was used, the reaction with β-aryl-substituted alkenyl B(pin) affords both isomers of products (Z and E, separable through column chromatography). Trapping experiments indicated the triplet energy transfer process was involved.
Supporting Information
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