Imidoyl chloride coupling reactions

It has been shown that the imidoyl chloride moiety of 2(lff)-pyrazinones can imdergo an easy addition/elimination reaction with alkyl amines [24], while reactions with anilines proceed under harsher conditions. Ullmann coupling [109-113] of 2(lff)-pyrazinones with substituted anilines could open the way to the libraries of physiologically active compounds useful in inhibiting HIV replication [7]. Polymer-bound pyrazinone was successfully... 

Recently, Olsson and coworkers have reported a cross-coupling reaction between seven-membered cyclic imidoyl chlorides and alkyl Grignard reagents (Scheme 36). The corresponding substimted imines, which are very difficult to prepare otherwise, are synthesized in good to excellent yields. 

Finally, imidoyl chloride can be transformed into the corresponding ketimines via palladium complex catalyzed cross-coupling reactions with alkynyltins (equation 16). ... 

The vast majority of C-C coupling reactions are catalysed by Pd phosphine complexes. Thus, electrogenerated allyl tin reagents couple with allyl halides307 or imidoyl chlorides,308 vinyl tin alkyls and aryldiazonium... 

A new synthesis of biologically important 1,4-benzodiazepines and 3-amino-1,4-benzodiazeprnes (56) using a Pdotalyzed cross-coupling reaction of imidoyl chlorides with a variety of functionalized organoboronates or boronic adds as the key step has been described by Nadin et al. [41]. Examples of C-C bond formations using Pd(0)-catalyzed reactions of imidoyl halides or triflates are surprisingly rare (Scheme 3.25). 

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