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Synlett 2023; 34(18): 2071-2084
DOI: 10.1055/a-2106-1799
DOI: 10.1055/a-2106-1799
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Modern Boron Chemistry: 60 Years of the Matteson Reaction
Transition-Metal-Free Insertion of Diazo Compounds, N-Arylsulfonylhydrazones or Ylides into Organoboronic Acids or Their Derivatives
The project is supported by the Natural Science Foundation of China (21871010) and the Laboratory for Synthetic Chemistry and Chemical Biology of Health@InnoHK, the Innovation and Technology Commission (ITC), Government of the Hong Kong Special Administrative Region (HKSAR).
Abstract
Insertion reactions of carbenes or ylides with organoboronic acids or their derivatives have emerged as valuable methods for coupling or homologation of organoboron compounds under metal-free conditions. The crucial steps of these reactions are coordination of the electron-rich carbon centers of the carbene precursors or ylides to the electron-poor boron center, followed by 1,2-migration of the corresponding tetracoordinated boron intermediates. This type of unique transformation provides an efficient method for the construction of C–C or C–X (X = H, B) bonds. Moreover, the C–B bonds generated by such transformations can be utilized as a handle for further derivatization or iterative homologations. In this Account, we summarize the developments in this arena according to the reactive diazo compound, N-arylsulfonylhydrazone or ylide species involved.
1 Introduction
2 Reactions with Diazo Compounds
3 Reactions with N-Arylsulfonylhydrazones
4 Reactions with Ylides
5 Conclusion
Publication History
Received: 16 May 2023
Accepted after revision: 05 June 2023
Accepted Manuscript online:
05 June 2023
Article published online:
09 August 2023
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