Unimolecular tetrakis-piperidine-4-ol: an efficient ligand for copper and amine free Sonogashira coupling

Abstract

A unimolecular tetrakis-piperidine-4-ol has been developed as an efficient ligand in combination with Pd/C for copper and amine free Sonogashira coupling. Various aryl and heteroaryl iodides were successfully coupled with aliphatic and aromatic alkynes to give internal alkynes in good to excellent yields.

(−)‐β‐Pinene‐based π‐Allylpalladium Complex‐Catalyzed Asymmetric Allylation of Bis‐Imines

“…Hence, these are envisioned as privileged precursors for the synthesis of N ‐heterocycles and other important building blocks . In this context, we also reported the utility of homoallylamines in domino aza‐Prins aza‐Cope cyclization and the products were further explored in cross‐coupling reactions . We continued with the development of new dimeric η 3 ‐bis‐π‐allylpalladium complexes based on (−)‐menthol .…”

Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide

“…The combination of Pd(TFA) 2 and other ligands such as dppbz, dppf, and Xantphos afforded the desired product in good yields, although the yields were lower than those obtained with Pd(TFA) 2 and dppp (entries 10-12). A number of oxidants were tested instead of Cu(OAc) 2 , but they did not give satisfactory results (entries [13][14][15][16][17][18]. The reaction gave much lower yields when carried out in solvents such as DMSO, diglyme, and toluene as compared to that in DMF (entries 19-21).…”

“…Hept-1-yn-1-ylbenzene (3s) 15 Oct-2-ynoic acid (1r; 462.6 mg, 3.3 mmol) and 2b (516.6 mg, 3.0 mmol) afforded 3s (439.3 mg, 2.55 mmol, 85%); colorless oil.…”