Matsuda-Heck coupling

Keywords Arenediazonium tetrafluoroborate salts, olefins, palladium acetate, triton X-100, water, room temperature, Pd-nanoparticles, Matsuda-Heck coupling, arylation of olefins, stereoselectivity, aryl substituted olefins... 

Table 5. Yields obtained for Matsuda Heck coupling between the p-methoxyphenyl diazonium salt and 2, 3-dihydrofurane using Pd2(dba)s.CHCl3 or [Pyr]2[PdCU] as catalyst (1 % mol) in microemulsions I, II, IE and IV formed with bnPyrNTf2 (on line (a) of Figure 8) at 27°C. Standard deviation on yields was around 2%.

One of the first examples of a Pd-catalyzed coupling reaction realized on an industrial scale is the Matsuda-Heck reaction of an aryl diazonium salt with 1,1,1-trifluoropropene developed by Baumeister and co-workers at Ciba-Geigy and today performed on ton scale by Novartis for the synthesis of a sulfonylurea herbicide (Prosulfuron). By combining three synthetic steps (diazotization, aUcenylation, and hydrogenation) in a... 

Thiophenediazonium salts 163 can be utiUzed as electrophilic coupling partners for differently functionaUzed alkenes 164 via a Matsuda-Heck (Scheme 64, left) as well as various potassium aryltrifluoroborates via Suzuki-Miyaura (Scheme 64, right) cross-coupling reactions giving rise to 3-substituted thiophenes 165 and 166... 

The Heck-type cross-coupling reactions can also be performed with aryldiazo-nium salts [247,273-278] (frequently called the Matsuda or Heck-Matsuda reaction), N-nitroso-N-arylacetamides [248], and hypervalent iodo compounds [250] at room temperature. 

In 2012, Gholinejad reported the Heck-Matsuda reaction (as well as the Suzuki-Miyaura reaction) using palladium nanoparticles [97]. The nanoparticles were supported on agarose beads, and at a loading of 2.6 pmol a variety of aryl ditizonium tetrafluoroborate salts could be coupled with... 

Diazonium salts are very useful starting materials for Heck reactions and other cross-coupling reactions (see 4.2.2). The first protocols have been developed by Matsuda and colleagues, and the reaction sometimes is being called Heck-Matsuda reaction. Since the 1970 s, a number of applications have emerged. Moro et al. used an arenediazonium salt in a Heck arylation reaction to obtain the resulting trans-stilbene derivative in excellent yield with complete stereocontrol (Scheme 5-18). ... 

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