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author:

Wang Biyu (Wang Biyu.) [1] (Scholars:王碧玉) | Ni Peizhong (Ni Peizhong.) [2] | Fan Jili (Fan Jili.) [3] | Zheng Huidong (Zheng Huidong.) [4] (Scholars:郑辉东) | Zhao Suying (Zhao Suying.) [5] (Scholars:赵素英) | Bai Zhengshuai (Bai Zhengshuai.) [6] (Scholars:白正帅)

Indexed by:

Scopus SCIE PKU CSCD

Abstract:

The synthesis of 3-tert-butyl-2-hydroxy-5-(pyridin-4-yl)benzaldehyde by Suzuki cross coupling reaction of 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde with pyridin-4-ylboronic acid was studied by using different catalysts [Pd(dppf)(2)Cl-2, Pd(OAc)(2) and Pd(PPh3)(4)], bases (Na2CO3, NaHCO3, K2CO3, K3PO4, Cs2CO3 and CsF) and solvents (DME/H2O, DMF/H2O and dioxane/H2O) under different temperature of 70, 80 and 100 degrees C. A compatible method was developed for the coupling reaction of arylboronic acids (having electron donating or withdrawing group) with aryl bromides (having electron withdrawing group). Under the condition of Pd(PPh3)(4), K2CO3, dioxane/H2O (V : V=4 : 1), 80 degrees C, the yield is excellent (97%) and the product separation is easy. The compatibility for aryl bromides with electron donating group is moderate.

Keyword:

aryl bromide catalytic mechanism pyridylboronic acid Suzuki cross coupling reaction

Community:

  • [ 1 ] [Wang Biyu]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
  • [ 2 ] [Ni Peizhong]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
  • [ 3 ] [Fan Jili]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
  • [ 4 ] [Zheng Huidong]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
  • [ 5 ] [Zhao Suying]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
  • [ 6 ] [Bai Zhengshuai]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
  • [ 7 ] [Bai Zhengshuai]Fuzhou Univ, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350002, Peoples R China

Reprint 's Address:

  • 白正帅

    [Bai Zhengshuai]Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China

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Source :

CHINESE JOURNAL OF ORGANIC CHEMISTRY

ISSN: 0253-2786

CN: 31-1321/O6

Year: 2014

Issue: 12

Volume: 34

Page: 2471-2477

0 . 9 9 1

JCR@2014

1 . 8 0 0

JCR@2023

ESI Discipline: CHEMISTRY;

ESI HC Threshold:268

JCR Journal Grade:3

CAS Journal Grade:4

Cited Count:

WoS CC Cited Count: 2

SCOPUS Cited Count: 3

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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