Palladium-catalyzed direct asymmetric C–H bond functionalization enabled by the directing group strategy

Abstract

<p>In the past decade, the selective C-C and C-heteroatom bond construction through the palladium-catalyzed direct C-H bond functionalization has been extensively studied by employing a variety of directing groups. Within...</p>

Ligand-promoted palladium-catalyzed β-methylene C–H arylation of primary aldehydes

“… 10 The TDG was found to play a similar role to that of the oxime directing group by binding to the substrate via reversible imine formation, upon which, it assists in the assembly of a stable palladacycle, effectively functionalizing the β-position. 11 Since the binding of the TDG is reversible and temporary, it is automatically removed upon functionalization, yielding an efficient and step-economic transformation. This work was succeeded by many other reports that expanded the reaction and the TDG scopes.…”

Three catalysts tango with olefins

“…Over the past two decades, many strategies for directly functionalizing C-H bonds have been developed. For instance, transition-metal catalysis has been used to functionalize alkyl and allylic C-H bonds, often with the assistance of directing groups 1,2 . However, these strategies are typically limited by the necessity of using pre-activated starting materials.…”

Diastereoselective palladium-catalyzed functionalization of prochiral C(sp3)–H bonds of aliphatic and alicyclic compounds

“…There exist notable efforts towards the enantioselective Pd( ii )-catalyzed, DG-aided, chiral ligand-enabled, C–H functionalization of methylene C(sp 3 )–H bonds, which leads to the generation of a single stereogenic center in target molecules. 16–19 This review mainly covers the diastereoselective, Pd( ii )-catalyzed, DG-aided functionalization of aliphatic compounds possessing the prochiral C(sp 3 )–H bonds, which allow for the generation of another stereogenic center and stereo-arrays in target molecules. The developments concerned with functionalizing the prochiral C(sp 3 )–H bonds of aliphatic compounds by using monodentate, bidentate, native, and transient DGs are discussed here.…”