Phosphinito palladium(ii) complexes as catalysts for the synthesis of 1,3-enynes, aromatic alkynes and ynones

Abstract

An air-stable phosphinito palladium(ii) complex has been found to be an efficient catalyst in the formation of C–C bonds.

Coordination chemistry and catalysis with secondary phosphine oxides

“…The first reports of the area are due to Li and coworkers at DuPont and date back to 2001. 30,156 They showed that the Pd-SPO complexes These results spurred a fruitful research in Pd-catalysed (and also Ni-catalysed) crosscouplings: Suzuki-Miyaura couplings 35,172,174,[214][215][216][217][218][219] but Mizoroki-Heck, 157,159,175,[220][221][222] Stille, 157,223 Sonogashira, 224,225 Hiyama, 226,227 Kumada-Tamao-Corriu, 31,[228][229][230] Negishi, 155,231 and other reactions with mechanisms related to cross-coupling reactions. 155,175,225,230,[232][233][234][235][236] In many of the cases but not all, 35,172,174,175,[220][221][222]225,…”

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

“…The use of terminal alkynes, activated by catalysts, as building blocks or intermediates in the synthesis of a large number of chemicals is extensively summarized in recent reviews [ 1 – 3 ]. The recently published papers confirm the present interest in the chemistry of terminal alkynes, e.g., in the synthesis of sulfinamides and isothiazoles [ 4 ], 1,3-enynes [ 5 ], α-monosubstituted propargylamines [ 6 ], 2-substituted pyrazolo[5,1- a ]isoquinolines [ 7 ], etc.…”

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

“…Very recently, Cardenas [44] proposed an air stable phosphinito palladium(II) complex ( Figure 4) as efficient catalyst for ynone synthesis via acyl Sonogashira reactions. Optimized reaction conditions required 5 mol % of the catalyst, 80 °C and Et3N for 18 h. When the reactions were carried out with microwave heating, similar high yields (81%-93%) were obtained in 1 h.…”

“…Very recently, Cardenas [44] proposed an air stable phosphinito palladium(II) complex ( Figure 4) as efficient catalyst for ynone synthesis via acyl Sonogashira reactions. Optimized reaction conditions required 5 mol % of the catalyst, 80 • C and Et 3 N for 18 h. When the reactions were carried out with microwave heating, similar high yields (81%-93%) were obtained in 1 h. Vasilyev et al [43] investigated the catalytic activity of four different palladium acyclic diaminocarbene complexes in the cross-coupling reactions of phenylacetylenes with aroyl chlorides.…”