A nickel/organoboron catalyzed metallaphotoredox platform for C(sp²)–P and C(sp²)–S bond construction

Abstract

Herein, an organoboron photocatalyst, aminoquinolate diarylboron (AQDAB), is utilized collaboratively with nickel catalyst in metallaphotoredox catalyzed C(sp2)–P and C(sp2)–S cross-coupling reactions. This strategy effectively couples aryl halides with diarylphosphine oxides...

Visible Light-Mediated Organoboron-Catalyzed Metal-Free Synthesis of Silanols from Silanes

“…Subsequently, He and Zhang reported the conversion of silane to silanol using eosin Y as a photocatalyst [ 34 ]. The study of photoinduced synthesis of silanol inspired us to consider whether the photocatalyst aminoquinolate B,B-diphenyl complex AQDAB [ 39 , 40 ], which was developed by our group and applied in photooxidation reactions [ 40 , 41 , 42 ], could induce such transformations. Herein, the success of this hypothesis is reported.…”

Organoboron/iodide-catalyzed photoredox N-functionalization of NH-sulfoximines/sulfonimidamides

“…13 Despite the remarkable achievements of octahedral Ru( ii ) or Ir( iii )-polypyridyl photocatalysts, 14 the development of purely organic photocatalysts without (precious) metals is still desirable from cost-effective, sustainable and residual metal perspectives. In this context, our group has developed a boron-based photocatalyst that has been successfully employed in a series of visible-light-induced transformations, such as dual Ni/photoredox catalyzed C–O, 15 C–P and C–S 16 bond constructions and photooxidation. 17 To further investigate the application of this boron-based photocatalyst and due to our continuous interest in organosulfur chemistry, 18 we wondered whether this photocatalyst could realize the N -functionalization of NH-sulfoximines.…”

Access to Polysubstituted Halophosphorylated Dihydrofurans via Halotrimethylsilane-Promoted Cascade Cyclization of γ-Hydroxyl Ynones with Diphenylphosphine Oxides

“…The classical synthetic methods have generally relied on coupling reactions of equivalent metal phosphorus reagents and aryl halides . Modern organic chemists have worked persistently for the advancement of new procedures for the introduction of phosphorus-containing groups in radical phosphorylation methodologies and transition-metal-catalyzed coupling approaches . Still, it is currently relatively difficult to simultaneously introduce an extra functional group during phosphorylation to accomplish difunctionalization.…”