Heck–Matsuda reaction of arenediazonium salts in water

ChemInform Abstract: Oxime‐Derived Palladacycles: Applications in Catalysis

“…Ethyl vinyl ketone, acrylates, ethyl crotonate, styrenes,a nd cyclopentene The HM reaction can also be performedi nw ater with different substituted arenediazonium tetrafluoroborates. [62] Acrylic derivatives, styrenes, allyl acetate, and but-3-en-2-ol have been used as alkenes, giving the arylated products in moderate to high yields [Scheme 12, Eq. (b)].…”

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

“…The reaction doesn't work well with electron-poor arenediazonium salts nor with severely sterically hindered arenediazonium salts [19a]. This reaction has recently been performed in neat water by Nájera's group [95]. Alternative solvents have been developed for the Heck-Matsuda reaction.…”

“…4-Methoxyphenyldiazonium tetrafluoroborate (0.054 g, 0.5 mmol) is placed in a flask with Pd(OAc) 2 (1.1 mg, 5 μmol, 1 mol%) and water (5 ml) [95]. Acrylic acid (0.054 g, 0.75 mmol) is added and the mixture stirred at room temperature for 16 h. The reaction mixture is extracted with CH 2 Cl 2 (10 ml) and the organic layer is filtered through a celite pad, and then dried with anhydrous NaSO 4 .…”

“…26 A cross-section of products successfully prepared by the Heck-Matsuda reaction in neat water[95]. 27 Attempts by Correia's group[96] at developing an asymmetric Heck-Matsuda reaction in chiral RTILs leading to (R,S)-paroxetine.…”

Carboxymethylcellulose‐supported palladium nanoparticles generated in situ from palladium(II) carboxymethylcellulose as an efficient and reusable catalyst for ligand‐ and base‐free Heck–Matsuda and Suzuki–Miyaura couplings

“…Recently, the progress of Heck–Matsuda and/or Suzuki–Miyaura reactions using aryldiazonium salts in the formation of carbon–carbon bonds has been reviewed. The traditional procedure for a Heck–Matsuda reaction generally involves catalysis using homogeneous palladium complexes including Pd(dba) 2 , 4b) Pd 2 (dba) 3 , Pd(OAc) 2 , PdCl 2 (CH 3 CN) 2 , Pd(TFA) 2 /chiral bisoxazoline ligand, palladacycle, Pd–NHC complex, Pd–phosphinous acid complexes, and so on. Pioneering studies of the Suzuki–Miyaura coupling of aryldiazonium salts with boronic acids were reported in 1996 by Genêt and co‐workers using Pd(OAc) 2 as catalyst .…”