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7.1. C-H Arylation with Prefunctionalized Arylating Reagents A first key development in 2005 was the demonstration that Pd(OAc)2 catalyzes the ortho-phenylation of diverse arylpyridines, quinolines, pyrrolidinones, oxazolidinones, and benzodiazepines with diphenyliodonium salts (Scheme 25).71-73 The unsymmetrical mesityl/aryl-substituted iodonium reagents [MessI-Ar]BF4 could be used to install different aryl groups (eq 29). The large mesityl substituents served as “dummy ligands” on the iodine(III), and the smaller aryl group was transferred with high selectivity (>99:1 in most cases). Generally, faster reaction rates and higher yields were observed with electron-deficient aryl groups. Several key experiments provided support for the mechanism in Scheme 26.17 First, the catalytic reaction showed a firstorder dependence on [IIII] (26), a second-order dependence on [Pd], and an inverse third-order dependence on [arylpyridine] (all consistent with the rate law derived for the sequence in Scheme 26). Second, Hammett studies with para-substituted IIII reagents showed a F value of +1.7, consistent with turnover-limiting oxidative addition. Finally, substitution of the ortho-C-H bond with a CsD bond resulted in an intra- but not an intermolecular kinetic isotope effect, indicating that C-H activation occurs after the turnover-limiting step. |
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