analysis and to construct new bonds in a straightforward manner. However, in these
pioneering studies, stoichiometric amounts of metal were necessary to perform the
key transformations. Subsequent efforts were devoted to the development of catalytic methods that retain synthetic applicability.
2.2 β-Arylation of Carbonyl Compounds
In 2005, taking advantage of bidentate coordinating groups to efficiently bind to a
transition metal and to position the latter in proximity to a targeted C–H bond,
Daugulis and co-workers described the Pd
II -catalyzed regioselective β- and
γ-arylation of unactivated C(sp
3 )–H bonds, by introducing respectively
8-aminoquinoline and picolinamide directing groups [20, 21]. Inspired by this
seminal report, numerous developments of new bidentate directing groups and
methods have been subsequently reported [22].
In 2006, the group of Corey described a first extension of this concept
[23]. Using the 8-aminoquinoline directing group, they could achieve the
palladium-catalyzed diastereoselective β- and γ-C(sp
3 )–H arylation of protected
α-amino acid derivatives with aryl iodides and catalytic amounts of Pd(OAc) 2 .
Scheme 2 Synthesis of the core of teleocidin B-4 via multiple Pd-mediated C–H activation
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