Copper-Catalyzed Phosphorylation of 2,3-Allenoic Acids and Phosphine Oxide: Access to Phosphorylated Butenolides

Abstract

We investigated a novel Cu-catalyzed annulation of 2,3-allenoic acids with diphenylphosphine oxide, leading to the formation of 4-phosphate butenolides in up to 88% yield. The formation of the C–P bond provides new avenues for the functionalization of different furan-2­(5H)-ones, with favorable features such as suitable functional group tolerance and mild synthesis conditions.

Photoinduced Three-Component Difluoroamidosulfonylation/Bicyclization: A Route to Dihydrobenzofuran Derivatives

“…Over the past few decades, a three-component methodology that uses easily handled DABCO·(SO 2 ) 2 as a convenient sulfur dioxide surrogate for the installation of a sulfonyl group has received increased attention . Therefore, with our ongoing studies on radical cyclization, we disclose the visible-light-induced three-component radical tandem bicyclization of N -allylbromodifluoroacetamides and terminal alkynes with the insertion of sulfur dioxide under external-oxidant-free and photocatalyst-free conditions.…”

Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins

“…Lactone derivatives, as versatile important structural building motifs, are widely found in natural products and biologically active compounds. 1 Similarly, isocoumarin derivatives have garnered the attention of researchers due to their broad pharmacological applications, 2 which include antifungal, 3 anti-allergic, 4 and anticoagulant activities, 5 and so on. 6 As shown in Fig.…”

Photoredox-Catalyzed Phosphonocarboxylation of Allenes with Phosphine Oxides and CO2

“…Consequently, phosphorus radical-mediated approaches have been a powerful tool for facile access to valuable phosphorus-containing scaffolds, which are widely applied in materials science, medicinal chemistry, and organic synthesis . While there has been only one report on the transformation of allenes and SPOs, in 2021 Yu’s group developed copper-catalyzed phosphorus radical-initiated cascade cyclization of 2,3-allenoic acids and SPOs to generate 4-phosphate butenolides, in which the oxidation of the phosphorylated allyl radical to the corresponding allyl cation was the key process (Scheme b). Both phosphonyl and carboxyl groups are valuable functional groups.…”