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author:

Li, Xue (Li, Xue.) [1] | Chen, Haohua (Chen, Haohua.) [2] | Wang, Hao (Wang, Hao.) [3] | Zhang, Qiaohui (Zhang, Qiaohui.) [4] | Sheng, Heyun (Sheng, Heyun.) [5] | Lan, Yu (Lan, Yu.) [6] | Song, Qiuling (Song, Qiuling.) [7] (Scholars:宋秋玲)

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ESCI

Abstract:

Suzuki-type cross-coupling is one of the most common strategies for the construction of C-C bonds. Despite great progress on the preparation of C(sp(2))-C(sp(2)) bonds, C(sp(2))-C(sp(3)) cross-coupling with aliphatic halides remains rare, especially with tertiary aliphatic halides and under transition-metal-free conditions. Here we report an efficient C(sp(2))-C(sp(3)) cross-coupling between alpha-(pseudo)halo aliphatic ketones and arylboronic acids via a 1,4-metallate shift. The alpha-arylated ketones obtained from this protocol under transition-metal-free and additive-free conditions in the presence of base are formed when the key intermediate enolate traps the arylboronic acid, leading to a tetracoordinate boron intermediate. A subsequent 1,4-metallate shift affords the Suzuki-type coupling products. This strategy provides a practical, scalable and operationally straightforward method for the synthesis of C(sp(2))-C(sp(3)) bonds, and is compatible with challenging tertiary aliphatic halides, allowing for the preparation of 1,3-disubstituted target products.

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Community:

  • [ 1 ] [Li, Xue]Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, Xiamen, Peoples R China
  • [ 2 ] [Wang, Hao]Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, Xiamen, Peoples R China
  • [ 3 ] [Zhang, Qiaohui]Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, Xiamen, Peoples R China
  • [ 4 ] [Sheng, Heyun]Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, Xiamen, Peoples R China
  • [ 5 ] [Song, Qiuling]Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, Xiamen, Peoples R China
  • [ 6 ] [Chen, Haohua]Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Xinxiang, Peoples R China
  • [ 7 ] [Lan, Yu]Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Xinxiang, Peoples R China
  • [ 8 ] [Song, Qiuling]Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Xinxiang, Peoples R China
  • [ 9 ] [Lan, Yu]Chongqing Univ, Sch Chem & Chem Engn, Chongqing Key Lab Theoret & Computat Chem, Chongqing, Peoples R China
  • [ 10 ] [Lan, Yu]Zhengzhou Univ, Coll Chem, Zhengzhou, Peoples R China
  • [ 11 ] [Lan, Yu]Zhengzhou Univ, Inst Green Catalysis, Zhengzhou, Peoples R China
  • [ 12 ] [Song, Qiuling]Fuzhou Univ, Fujian Prov Univ, Key Lab Mol Synth & Funct Discovery, Coll Chem, Fuzhou, Peoples R China

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Source :

NATURE SYNTHESIS

ISSN: 2731-0582

Year: 2023

Issue: 12

Volume: 2

Page: 1211-1221

1 7 . 5

JCR@2023

1 7 . 5 0 0

JCR@2023

JCR Journal Grade:1

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 7

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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