Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling

Abstract

The traditional transition metal-catalyzed cross-coupling reaction, although well suited for C(sp2)-C(sp2) cross-coupling, has proven less amenable toward coupling of C(sp3)-hybridized centers, particularly using functional group tolerant reagents and reaction conditions. The development of photoredox/Ni dual catalytic methods for cross-coupling has opened new vistas for the construction of carbon-carbon bonds at C(sp3)-hybridized centers. In this chapter, a general outline of the features of such processes is detailed.

Formal Giese addition of C(sp3)–H nucleophiles enabled by visible light mediated Ni catalysis of triplet enone diradicals

“… 3 We therefore postulated that such a new reactivity could potentially be realized by adopting recent advances in visible light-mediated nickel catalysis. 4 …”

Synthesis of Non‐Classical Arylated C‐Saccharides through Nickel/Photoredox Dual Catalysis

“…In recent years, photoredox/nickel cross-coupling reactions have drawn extensive attention from the chemistry community. 15 Such processes allow the cross-coupling of Csp 3 nucleophiles under mild conditions by invoking a single-electron transmetalation pathway. Taking advantage of these modular and operationally simple conditions would allow access to virtually unexplored, non-classical, arylated saccharides.…”

Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

“…These include cross-electrophile “reductive” couplings that use an exogenous, stoichiometric reductant to shuttle electrons to the nickel catalyst, 5 as well as cross-coupling reactions that rely on synergistic reactivity between nickel and photoredox co-catalysts. 6 Taken together, these reactions enable the cross-coupling of a broad range of C(sp 3 ) substrates, providing access to a variety of products.…”