Rhodium-catalysed direct formylmethylation using vinylene carbonate and sequential dehydrogenative esterification

Abstract

A rhodium-catalysed direct formylmethylation adopting vinylene carbonate as an ethynol equivalent is reported. The developed catalytic system is further utilised for the oxidant-free production of esters with the liberation of...

Ruthenium‐Catalyzed Vinylene Carbonate Annulation by C−H/N−H Functionalizations: Step‐Economical Access to Indoles

“…other additives were far less efficient. Moreover, the additive Zn(OAc) 2 could significantly improve this yield, while the other acetate or triflate salts such as Cu(OAc) 2 , AgOAc, KOAc, and Zn(OTf) 2 that frequently used in Ru(II) catalysis, resulted in unsatisfactory yields (entries [15][16][17][18][19]. Moreover, decreasing the reaction temperature to 80 °C and 60 °C, the desired product was obtained in 89% and 81% yield respectively (entries 20 and 21).…”

“…[14] Afterwards, Miura developed an rhodium-catalyzed directing-group-assisted CÀ H formylmethylation using vinylene carbonate as an ethynol equivalent. [15] To further explore and enrich annulative synthesis of indoles, we herein, report the first carboxylateassisted inexpensive ruthenium-catalyzed [16] oxidative annulations of vinylene carbonate for the preparation of indoles through CÀ H/NÀ H bond functionalization. (Scheme 1d).…”

Rh(III)-Catalyzed Synthesis of Indazolo[2,3-a]quinolines: Vinylene Carbonate as C1 and C2 Building Blocks

“…Afterward, vinylene carbonate was employed as the acetyl transfer reagent resulting in the formation of 4-methylpyrrolo-quinoxalines and 4-methylquinazolines, in which vinylene carbonate served as a C1 synthon in cyclization (Scheme c). Although there has been prominent research on vinylene carbonate, the application of vinylene carbonate in constructing structurally diverse nonsubstituted polyheterocycles is still in its infancy . Therefore, it is significant to explore novel catalytic systems to breakthrough its limitation in organic synthesis and provide interesting molecules.…”

Ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles: access to fused anthranils

“…9 Miura and co-workers reported the direct formylmethylation of arenes bearing pyrazoles as the directing group. 10 This reaction was also elaborated with N -pyrimidyl indolines and N -pyrimidyl pyrroles to afford the corresponding formylmethylated products with moderate to good yields. Notably, when the reactions were carried out in methanol, the formation of the corresponding esters was observed (Scheme 1c).…”