1. Reactivities of α‐Oxo BMIDA Gold Carbenes Generated by Gold‐Catalyzed Oxidation of BMIDA‐Terminated Alkynes
- Author
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Zheng, Yang, Jiang, Jingxing, Li, Yue, Wei, Yongliang, Zhang, Junqi, Hu, Jundie, Ke, Zhuofeng, Xu, Xinfang, and Zhang, Liming
- Subjects
Inorganic Chemistry ,Organic Chemistry ,Chemical Sciences ,Alkynes ,C-H Insertion ,Carbenes ,Gold Catalysis ,alpha-Boryl Ketones ,C−H Insertion ,α-Boryl Ketones ,Chemical sciences - Abstract
An oxidative strategy is reported to access α-oxo BMIDA gold carbenes directly from BMIDA-terminated alkynes. Besides offering expedient access to seldom studied boryl metal carbenes, these BMIDA gold carbene species undergo facile insertions into methyl, methylene, methine, and benzylic C-H bonds in the absence of the Thorpe-Ingold effect. They also undergo efficient OH insertion, cyclopropanation, and F-C alkylations. This chemistry provides rapid access to structurally diverse α-BMIDA ketones, which are scarcely documented. In combination with DFT studies, the role of BMIDA is established to be an electron-donating group that attenuates the high electrophilicity of the gold carbene center.
- Published
- 2023