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author:

An, Hejun (An, Hejun.) [1] | Zhu, Wei (Zhu, Wei.) [2] | Tan, Mengwei (Tan, Mengwei.) [3] | Cai, Meihui (Cai, Meihui.) [4] | Huang, Yi (Huang, Yi.) [5] | Ma, Xingxing (Ma, Xingxing.) [6] | Song, Qiuling (Song, Qiuling.) [7]

Indexed by:

Scopus SCIE

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 equivalent to 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.

Keyword:

distinct electrophile dual migrations multi-substituted olefins tetracoordinate borons

Community:

  • [ 1 ] [An, Hejun]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 2 ] [Zhu, Wei]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 3 ] [Tan, Mengwei]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 4 ] [Cai, Meihui]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 5 ] [Huang, Yi]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 6 ] [Ma, Xingxing]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 7 ] [Song, Qiuling]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
  • [ 8 ] [Ma, Xingxing]Hubei Normal Univ, Coll Chem & Chem Engn, Hubei Key Lab Pollutant Anal & Reuse Technol, Huangshi 435002, Peoples R China
  • [ 9 ] [Song, Qiuling]Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
  • [ 10 ] [Song, Qiuling]Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

Reprint 's Address:

  • 宋秋玲

    [Ma, Xingxing]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China;;[Song, Qiuling]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China;;[Ma, Xingxing]Hubei Normal Univ, Coll Chem & Chem Engn, Hubei Key Lab Pollutant Anal & Reuse Technol, Huangshi 435002, Peoples R China;;[Song, Qiuling]Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China;;[Song, Qiuling]Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

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Source :

SCIENCE CHINA-CHEMISTRY

ISSN: 1674-7291

Year: 2025

1 0 . 4 0 0

JCR@2023

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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