A rhodium(III)-catalyzed
C–H allylation of (hetero)arenes
by using 2-methylidenetrimethylene carbonate as an efficient allylic
source has been developed for the first time. Five different directing
groups including oxime, N-nitroso, purine, pyridine,
and pyrimidine were compatible, delivering various branched allylarenes
bearing an allylic hydroxyl group in moderate to excellent yields.
Herein, Rh(III)-catalyzed C4-selective CÀ H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished.
A synthetic method for quinoxaline derivatives from the [4+2] annulation of β‐keto sulfoxonium ylides and o‐phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional‐group compatibility. Moreover, this cyclization strategy was successfully applied in late‐stage modification for structurally complex bioactive compounds.
In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides and N‐carbamoylindoles with vinylene carbonate was accomplished, which afforded a series of naphthalenones containing a β‐ketosulfoxonium ylide moiety, isocoumarins, and pyrimidones. This protocol featured mild conditions, broad substrate scope, and functional‐groups compatibility. In addition, related applications and preliminary mechanistic exploratory were also investigated
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