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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.
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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
Affiliated Colleges: