Benzyltrioctylammonium chloride

The acylpalladium halide complex 84 is an intermediate of catalytic decarbony-lation of aroyl halides 83 [53]. The decarbonylation of 84 generates the aryl-palladium intermediate 85 at higher temperature which undergoes facile alkene insertion. Therefore, similar to aryl halides, acyl halides can be used for the alkene insertion. The reaction is carried out with a phosphine-free Pd catalyst in the presence of tertiary amines [54]. Higher yields were obtained by using a mixture of K2CO3 and benzyltrioctylammonium chloride [55]. 

Although aryl halides and triflates are the most commonly used arylating agents, there are successful examples where both aroyl chlorides and arylsulfonyl chlorides have been employed. Pd-catalyzed decarbonylations and desulfonylations and subsequent Heck couplings are often conducted with trialkylamines such as A-ethylmorpholine as a base, but improved yields are reported in cases in which the tertiary amine is replaced by a mixture of potassium carbonate and benzyltrioctylammonium chloride. In Table 2 two examples are given (entries 17 and 18). ... 

A mixture of 1-naphthalenesulfonyl chloride, /i-butyl acrylate, K2CO3, and catalytic amounts of bis(benzonitrile)dichloropalladium(II) and benzyltrioctylammonium chloride in m-xylene stirred at 140° for 4 h under N2 butyl 3-(l-naphthyl)-2-prope-noate. Y 90%. F.e.s. M. Miura et al.. Tetrahedron Letters 30, 975-6 (1989). 

Benzyltriethylammonium chloride s. under NaOH Benzyltrioctylammonium chloride s. under PdCl2(PhCN)2... 

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