New pyrazole-tethered Schiffs bases as ligands for the Suzuki reaction

Tetrahedron Letters

Volumn 46, Issue 1, 2005, Pages 15-18

  Mukherjee, Anuradha ^a   Sarkar, Amitabha ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

N,N donor system; Pd; Pyrazole; Schiffs base; Suzuki coupling

Indexed keywords

BENZENEBORONIC ACID; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; LIGAND; PYRAZOLE DERIVATIVE; SCHIFF BASE;

ARTICLE; CHEMICAL REACTION; SUZUKI REACTION;

LATEOLABRAX JAPONICUS;

EID: 10044227154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.051     Document Type: Article

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17. When 4-bromoanisole and phenylboronic acid were treated with N-phenylpyrazole as the ligand instead of ligand 2, below 65°C, no coupling was observed. Above 65°C rapid precipitation of Pd-black was observed.
18. General procedure for synthesizing ligands 2: the pyrazole-tethered aldehyde (1 equiv) and aromatic amine (1 equiv) in dry ethanol were refluxed in the presence of one drop of acetic acid until the starting material was completely consumed (monitored by TLC). After removal of solvent, the product was obtained either as a solid or a semi-solid, which was purified by crystallization using hot ethanol.
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20. 2 for this reaction
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