Pd-catalyzed direct C-H bond arylation as an efficient route for C-C bond has attracted significant attention in recent years. A series of direct C-H arylations with aryl halides have been reported based on a Pd(0)-PR3/Ar-X system. In 2005, dipenyliodonium salts were used for arylation of arenes. These reactions were proposed to proceed by a Pd(II)/Pd(IV) mechanism. Then the combination of Ag(I) salts and aryl iodides has been utilized for Pd-catalyzed arylation. In most of above reports directing groups exist in the arenes. We developed two efficient methods for direct arylation of electron-deficient fluoroarenes without directing groups (18 examples). One protocol did not employ an external ligand and other introduced monoprotected amino acid ligand (Ac-Ile-OH) to assist the reaction to proceed under mild conditions. And we presumed that C-H activation of simple arenes experiences the CMD (concerted metalation-deprotonation) process under the two conditions. Hence the selectivity is attributed to the variation in the acidity of C-H bonds and steric hindrance of arene substrates.

Pd(OAc)<sub>2</sub> catalyzed direct arylation of electron-deficient arenes without ligands or with monoprotected amino acid assistance

245th National Meeting (2013)

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Pd(OAc)2 catalyzed direct arylation of electron-deficient arenes without ligands or with monoprotected amino acid assistance

Pd(OAc)₂ catalyzed direct arylation of electron-deficient arenes without ligands or with monoprotected amino acid assistance