2012
DOI: 10.1002/aoc.2875
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Efficient salicylaldimine ligands for a palladium‐catalyzed Suzuki–Miyaura cross‐coupling reaction

Abstract: A series of salicylaldimine ligands were designed to promote palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. After a screening process, a ligand with a bulky 2,4-di-tert-butyl substituent on the salicyaldehyde backbone and cyclohexylamine moiety was found to serve as a good combination for this reaction in aqueous solutions of DMF. The protocol demonstrated a significant advance in the efficiency of the cross-coupling of aryl bromides and aryl chlorides with arylboronic acids to produce the desired… Show more

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Cited by 22 publications
(2 citation statements)
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“…However, the more inexpensive aryl chlorides have been rarely used as coupling partners because the activation of aryl chlorides is much more difficult than aryl bromides and iodides. To search for new catalysts that exhibit high activity and stability with a broad range of substrates in the coupling reaction, as part of our ongoing research interest in cross‐coupling with phosphine‐free ligands, we herein report a series of pyridylbenzamidine ligands (Fig. ) as phosphine‐free ligands for Suzuki–Miyaura reaction under aerobic conditions.…”
Section: Introductionmentioning
confidence: 99%
“…However, the more inexpensive aryl chlorides have been rarely used as coupling partners because the activation of aryl chlorides is much more difficult than aryl bromides and iodides. To search for new catalysts that exhibit high activity and stability with a broad range of substrates in the coupling reaction, as part of our ongoing research interest in cross‐coupling with phosphine‐free ligands, we herein report a series of pyridylbenzamidine ligands (Fig. ) as phosphine‐free ligands for Suzuki–Miyaura reaction under aerobic conditions.…”
Section: Introductionmentioning
confidence: 99%
“…1 When they are hybridised with a hemilabile donor pendant, the ligands can exhibit higher coordinative ability or flexibility, depending on the association state of the pendant. 2 The neutral ligands often require activation through deprotonation by e.g. Na, 3 NaH, 4 and NaR 5 before complexation can take place smoothly.…”
mentioning
confidence: 99%