Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization

Abstract

Organic carbonates are important and valuable building blocks in synthetic chemistry. Among them, vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C-H conversions...

Rh(III)‐Catalyzed C−H Annulation of 3‐Aryl‐2H‐benzo[e][1,2,4]thiadiazine‐1,1‐dioxides with Vinylene Carbonates

“…Therefore, the reaction was then conducted using [Cp*RhCl 2 ] 2 (3 mol %) in dichloroethane (DCE) at 100 °C. But the corresponding product 3 a was isolated only in 33 % yield (entry b, Table 1), which was fully characterized using 1 H & 13 C NMR and mass spectrometry.…”

“…[12] It has been successfully utilized as a source of acetyl and acetylene to perform the [4 + 1] or [4 + 2] and [3 + 2] CÀ H annulation reactions. [13] Miura et al, reported, for the first time the vinylene carbonate as an oxidizing acetylene surrogate to carry out CÀ H annulation reactions using Rh(III) catalysis. [14] Subsequently, Zhang et al developed an oxidative annulations of vinylene carbonate with benzamides and acrylamides.…”

Carboxylic Acid-Enabled Vinylene Transfer Reaction by Co(III) Catalyst: Scope and Applications to the Five-Step Total Synthesis of Protoberberine Alkaloids Containing Free Hydroxyl Group without Protection

“…Seminal work reported by Miura and co-workers in 2019, which employed the Rh­(III) complex to facilitate the vinylene transfer event, initiated this chemistry (Figure B) . Thereafter, a number of vinylene transfer reactions catalyzed by Rh­(III), Ru­(II), and Co­(III) , were documented successively, providing a powerful toolbox to assemble small vinylene motifs to heterocyclic scaffolds that are otherwise difficult to be obtained by conventional methods (Figure C). ,− , …”

“…In the past few years, the transition-metal chemistry involving vinylene carbonate has witnessed a remarkable evolution. , In this context, vinylene transfer reactions by C–H activation delivering useful heterocyclic compounds gained extraordinary attention. Seminal work reported by Miura and co-workers in 2019, which employed the Rh­(III) complex to facilitate the vinylene transfer event, initiated this chemistry (Figure B) .…”

A zwitterionic fused-ring framework as a new platform for heat-resistant energetic materials

“…Recently, signicant focus on the development of high heatresistant energetic materials has been observed due to their widespread applications in the military, civil, and aerospace elds. [1][2][3][4][5] In the synthesis of highly heat-resistant energetic materials, the balance between stability and energy is crucial. [6][7][8] Many conventional heat-resistant energetic materials oen exhibit inadequate energetic performance limiting their broad applicability and hindering the development of technology in the elds of national defense and aerospace.…”