Although palladium-catalyzed transformations of activated C(sp3)�H bonds a to electron-withdrawing groups, such as ketones, esters, and amides, have been intensively studied, examples of intermolecular arylations of weakly acidic C(sp3)�H bonds (those with pKa > 30) in the absence of a directing group are quite scarce.  We report the palladium-catalyzed allylic substitution of toluene-derived pronucleophiles activated by tricarbonylchromium.  A variety of cyclic and acyclic allylic electrophiles can be employed with in situ generated nucleophiles from toluene to benzyl amine and ether derivatives (?6-C6H5�CH2Z)Cr(CO)3 (Z = H, CH3, Ar, NR2, OR).  We are also investigating a chromium-free direct arylation involving C(sp3)�H bond of diarylmethane derivatives. Both reactions provide substructures that are common structural motifs in bioactive compounds.

Palladium-catalyzed arylation and allylic substitution of weakly acidic benzylic C(sp<sup>3</sup>)–H bonds at room temperature

244th National Meeting (2012)

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Palladium-catalyzed arylation and allylic substitution of weakly acidic benzylic C(sp3)–H bonds at room temperature

Palladium-catalyzed arylation and allylic substitution of weakly acidic benzylic C(sp³)–H bonds at room temperature