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author:

An, H. (An, H..) [1] | Zhu, W. (Zhu, W..) [2] | Tan, M. (Tan, M..) [3] | Cai, M. (Cai, M..) [4] | Huang, Y. (Huang, Y..) [5] | Ma, X. (Ma, X..) [6] | Song, Q. (Song, Q..) [7]

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Abstract:

Herein, we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid (HCl) and N-chlorosuccinimide (NCS), which is significantly different from conventional migration modes under basic conditions. In this protocol, HCl, as the first electrophile, activates the C≡C bond, triggering the first 1,2-aryl migration. Subsequently, NCS promotes a secondary metallate shift, enabling the construction of polysubstituted alkenes. Notably, this process can work well under mild conditions, exhibits high efficiency, and provides valuable products. This transformation reveals that Zweifel olefination is not just limited to traditional basic conditions, it can proceed smoothly under acidic conditions as well, which greatly expands the scope of this well-known olefination reaction. © Science China Press 2025.

Keyword:

distinct electrophile dual migrations multi-substituted olefins tetracoordinate borons

Community:

  • [ 1 ] [An H.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 2 ] [Zhu W.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 3 ] [Tan M.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 4 ] [Cai M.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 5 ] [Huang Y.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 6 ] [Ma X.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 7 ] [Ma X.]Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, China
  • [ 8 ] [Song Q.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, 350108, China
  • [ 9 ] [Song Q.]State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China
  • [ 10 ] [Song Q.]Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Peking University, Beijing, 100871, China

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Source :

Science China Chemistry

ISSN: 1674-7291

Year: 2025

1 0 . 4 0 0

JCR@2023

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ESI Highly Cited Papers on the List: 0 Unfold All

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30 Days PV: 0

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