108604-35-9Relevant articles and documents
A green protocol for ligand, copper and base free Sonogashira cross-coupling reaction
Dewan, Anindita,Sarmah, Manashi,Bora, Utpal,Thakur, Ashim J.
, p. 3760 - 3763 (2016)
A convenient methodology has been developed for palladium catalyzed Sonogashira cross-coupling reaction under mild and green reaction conditions. The reaction is catalyzed by an in situ generated catalytic system based on Pd(OAc)2and WEB (water extract of banana peels ash) in the absence of any organic or inorganic base, ligand and copper salt with excellent yield of cross coupled product. The reaction condition is compatible with electronically diversified aryl iodides and electronically diversified aryl or aliphatic alkyne. The present method developed for the Sonogashira reaction offers many advantages including high conversion, high economy, the involvement of non-toxic green substrates, etc.
Effect of fluorine substituents on catalytic functionalizations of alkyl halides with organostannanes
Shimizu, Rie,Fuchikami, Takamasa
, p. 6891 - 6894 (2001)
Introduction of fluorine atom(s) at the γ- and δ-positions of alkyl iodides increased the selectivities toward palladium-catalyzed cross-coupling reaction with organostannanes. A similar effect of fluorine substituents on the selectivities was also observed in the palladium-catalyzed carbonylative coupling reaction of alkyl iodides with phenyltributyltin under CO pressure.
Urea as mild and efficient additive for palladium catalyzed Sonogashira cross coupling reaction
Sarmah, Manashi,Dewan, Anindita,Thakur, Ashim J.,Bora, Utpal
, p. 914 - 916 (2016)
A catalytic system based on Pd(OAc)2/urea has been developed for Sonogashira cross coupling of aryl halides with terminal alkynes at room temperature. This catalytic system effectively promotes Sonogashira coupling of both aryl iodides and aryl bromides to give polyfunctional alkynes under copper and amine free conditions. The catalytic system is readily accessible, inexpensive and highly flexible for both aromatic and aliphatic alkynes.
Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes
Zhang, Yang,Torker, Sebastian,Sigrist, Michel,Bregovi?, Nikola,Dydio, Pawe?
supporting information, p. 18251 - 18265 (2020/11/02)
Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.
Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF
Gauthier, Rapha?l,Mamone, Marius,Paquin, Jean-Fran?ois
supporting information, p. 9024 - 9027 (2019/11/14)
The gold-catalyzed hydrofluorination reaction of internal alkynes using hydrofluoric acid is reported. Notably, those conditions use one of the most economical sources of HF and are free of additional additives. Both symmetrical and unsymmetrical internal alkynes can be utilized, and the use of alkynes bearing a fluorinated group at the propargylic position as substrates allowed for a regioselective hydrofluorination reaction.