2009
DOI: 10.1002/jhet.27
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The synthesis and application of 2‐acetyl‐6‐(1‐naphthyl)‐pyridine oxime as a new ligand for palladium precatalyst in Suzuki coupling reaction

Abstract: in Wiley InterScience (www.interscience.wiley.com).The synthesis of 2-acetyl-6-(1-naphthyl)-pyridine oxime ligand from 2,6-dibromopyridine and 1-bromo-naphthalene is described, and the new palladium(II) complex used as a Pd(0) precatalyst in the Suzuki cross-coupling reaction was studied. The results showed that the novel naphthalene pyridine oxime complex could serve as an efficient precatalyst.

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Cited by 7 publications
(4 citation statements)
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“…A mixture of 1-[6-bromopyridin-2-yl]ethan-1-one 1 20 (1.00 g, 4.99 mmol), 2,4-difluorophenylboronic acid (0.95 g, 5.99 mmol), aqueous sodium carbonate (2 M, 5 mL), toluene (10 mL), ethanol (5 mL) was subjected to three freeze–pump–thaw cycles, followed by placing under argon. Tetrakis(triphenylphosphine)palladium(0) (0.23 g, 4 mol%) was added followed by one further freeze–pump–thaw cycle, backfilling with argon.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…A mixture of 1-[6-bromopyridin-2-yl]ethan-1-one 1 20 (1.00 g, 4.99 mmol), 2,4-difluorophenylboronic acid (0.95 g, 5.99 mmol), aqueous sodium carbonate (2 M, 5 mL), toluene (10 mL), ethanol (5 mL) was subjected to three freeze–pump–thaw cycles, followed by placing under argon. Tetrakis(triphenylphosphine)palladium(0) (0.23 g, 4 mol%) was added followed by one further freeze–pump–thaw cycle, backfilling with argon.…”
Section: Methodsmentioning
confidence: 99%
“…The synthesis of L 1 H required for D-Blue was achieved in a three-step procedure. Compound 2 was prepared by Suzuki coupling of 2,4-difluorophenyl boronic acid and 1-[6-bromopyridin-2-yl]ethan-1-one 20 in a yield of 86%. The Suzuki coupling was followed by a Claisen condensation and hydrazine cyclisation to give the ancillary ligand L 1 H in a yield of 48%.…”
Section: Introductionmentioning
confidence: 99%
“…The precursor ketone is not commercially available and has been synthesized using a variation of the previously reported Suzuki cross-coupling reaction of 1-naphthyl boronic acid with 2-bromo-6-acetylpyridine [61]. Compound L1dipp has been reported before [53,62], although no characterization data were disclosed.…”
Section: Synthetic and Structural Aspectsmentioning
confidence: 99%
“…The title compound was prepared using a modification of a previously reported procedure [61]. A flask was charged with 2-bromo-6-acetylpyridine (1.788 g, 8.94 mmol), tetrakis(triphenylphosphine) palladium(0) (0.207 g, 0.179 mmol, 2 mol %), 2M aqueous potassium carbonate (8.94 mL, 17.88 mmol, 2 eq.…”
Section: Synthesis Of 2-{cme=o}-6-(1-c10h7)c5h3nmentioning
confidence: 99%