17595-85-6Relevant academic research and scientific papers
A sustainable heterogenized palladium catalyst for Suzuki-Miyaura cross coupling reaction of azaheteroaryl halides in aqueous media
Ganesamoorthy,Muthu Tamizh,Shanmugasundaram,Karvembu
, p. 76 - 85 (2018/03/23)
A unique recyclable Pd catalyst (‘SiO2’-NH2-Pd) for Suzuki-Miyaura coupling reaction of azaheteroaryl halides is developed. The catalytic system is working under mild aqueous condition with low Pd loading and without the use of phosphine ligand. The plausible mechanism is proposed based on the formation of undesired symmetrical biaryl from the coupling reaction of azaheteroaryl chlorides due to the oxidative homocoupling of nucleophilic arylboronic acid. This catalytic system represents an attractive and promising approach for the synthesis of azaheterobiaryls with high product yields. The catalyst has demonstrated an excellent recyclability.
Negishi cross-coupling reaction catalyzed by an aliphatic, phosphine based pincer complex of palladium. biaryl formation via cationic pincer-type Pd IV intermediates
Gerber, Roman,Blacque, Olivier,Frech, Christian M.
experimental part, p. 8996 - 9003 (2011/10/31)
The aliphatic, phosphine-based pincer complex [(C10H 13-1,3-(CH2P(Cy2)2)Pd(Cl)] (1) is a highly active Negishi catalyst, enable to quantitatively couple various electronically activated, non-activated, deactivated, sterically hindered and functionalized aryl bromides with various diarylzinc reagents within short reaction times and low catalyst loadings. Experimental observations strongly indicate that a molecular mechanism is operative with initial chloride dissociation of 1 and formation of the cationic T-shaped 14e- complex [(C10H13-1,3-(CH2P(C6H 11)2)2)Pd]+ (B), which undergoes oxidative addition of an aryl bromide (Ar′Br) to yield the cationic, penta-coordinated aryl bromide pincer complexes of type [(C10H 13-1,3-(CH2P(Cy2)2)Pd(Br) (aryl′)]+ (C) with the metal center in the oxidation state of +IV and the aryl unit in cis position relative to the aliphatic pincer core. Subsequent transmetalation with Zn(aryl)2 result in the cationic diaryl pincer complexes of type [(C10H13-1,3-(CH 2P(Cy2)2)Pd(aryl)(aryl′)]+ (D), which reductively eliminate the coupling products, thereby regenerating the catalyst. The neutral square planar aryl pincer complex - a possible key intermediate in the catalytic cycle - was found to be reversibly formed in the reaction mixture but is not involved in the catalytic mechanism. Similarly, palladium nanoparticles as the catalytically active form of 1 could have been excluded. The Royal Society of Chemistry 2011.
Exploration of Ionic Liquids as Soluble Supports for Organic Synthesis. Demonstration with a Suzuki Coupling Reaction
Miao, Weishi,Chan, Tak Hang
, p. 5003 - 5005 (2007/10/03)
(Equation Presented) The efficiency of ionic liquid supported synthesis was demonstrated by the Suzuki reaction of ionic liquid supported iodobenzoate compounds with arylboronic acids in aqueous media to give, after cleavage with ammonia/methanol, biaryl products in good yields and high purities, without the need for chromatographic purification.
