Wanrong Dong

Photoredox catalyst-mediated direct regioselective phosphonylation of indoles

ABSTRACT An efficient hetero-cross-dehydrogenative-coupling (hetero-CDC) reaction between N-protected indoles and phosphites to 2-indolyphosphites is described. The regioselective methodology took place in the presence of photo redox catalyst Ru(bpy)3(PF6)2 combined with oxygen as an clean oxidant when exposed to visible light, furnishing the 2-indolyphosphites as the exclusive products in moderate to good yields with good functional group tolerance. Moreover, the phosphonylation protocol was proved by the control reaction to proceed through the radical pathway. GRAPHICAL ABSTRACT

Copper-Promoted Desulfitative N-Arylation of Sulfonamides and Sulfoximines with Sodium Arylsulfinates

A general and direct N-arylation of sulfonamides and NH-sulfoximines by sodium arylsulfinates through a desulfitative pathway was herein demonstrated. The reaction proceeded with catalytic loadings of Cu(II)-catalysts without any external ligands. And the novel arylation protocol featured for high efficiency (up to 93% yields) and good substituent tolerance (up to 53 examples). Moreover, a plausible reaction mechanism was also discussed.

Selective Tandem Inter/intramolecular Eglington Coupling for Chiral Cyclophyne Synthesis

Abstract Tandem inter- and intramolecular Eglington couplings take place with good selectivity to afford an enantiopure three-dimensional cyclophyne with a large cavity.

H2O2-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400

A green and practical protocol between sulfonyl hydrazides and disulfides is herein reported for the synthesis of unsymmetrical thiosulfonates with the assistance of H2O2 in PEG-400, releasing N2 and H2O as the byproducts. The efficient and compatible process was considered to take place in the absence of metallic catalysts through a radical mechanism as determined by EPR analysis.

Copper-catalyzed Oxidative Alkylation (Methylation) of Phosphonamides and Phosphinamides by Using Dicumyl Perxide

An effective and practical CuI-catalyzed methodology toward N-alkyl or N-methyl phosphonamides and phosphinamides was herein demonstrated. The transformation took place readily under the oxidative conditions, and plenty of N-alkylated (methylated) amides (30 examples) were successfully furnished in high efficiency (up to 92% yields). Dicumyl peroxide was considered to act either as the oxidant for the alkylation reaction or as methyl donator for the methylation protocol.

Preparations of N- and P-substituted acetylenes under metal-free conditions

ABSTRACT An efficient strategy towards triazole- or phosphine-oxide-substituted alkynes with the assistance of strong base LiHMDS is described. The facile and practical reaction took place from easily prepared substrates in a one-pot manner without participation of any transition metal catalysts or ligands, exhibiting good functional groups tolerance (up to 37 examples) and high efficiency (up to 90% yields). The isolation of the key intermediate proved the hypothesis of the proposed mechanism of the one-pot preparation. GRAPHICAL ABSTRACT

Iron-catalyzed deoxygenation and 2-sulfonylation of quinoline N-oxides by sodium sulfinates towards 2-sulfonyl quinolines

Abstract An iron(III)-catalyzed protocol towards 2-sulfonyl quinolines from quinoline N-oxides and sodium sulfinates was herein illustrated. The general and direct option featured for high efficiency (up to 91% yields) and good functional compatibilities (27 examples) in the Fe(III)-catalysis. Moreover, free radical mechanism was proposed for the one-pot deoxygenation and sulfonylation reaction based on the results of the control reactions. Graphical Abstract An novel reaction between quinoline N-oxides and sodium sulfinates for the synthesis of 2-sulfonyl quinolines was herein achieved by an iron(III)-catalyzed system. The general and direct transformation exhibited high efficiency (up to 91% yields) and good functional-groups compatibilities (27 examples). Moreover, free radical mechanism was proposed for the one-pot deoxygenation and sulfonylation reaction based on the results of the control reactions.

RhIII-catalyzed annulation of N-methoxyindozamides with heterobicyclic alkenes towards indolo[3,2-c]heteroarenes

Abstract A rhodium-catalyzed annulation protocol towards indolo[3,2-c]-1-azaanthraenes and successive treatment with different acids, which offered diverse indolo[3,2-c]-heteroarenes, were herein demonstrated. The transition metal-mediated system offered a direct and facile approach towards the heterocyclic compounds of great significance, enjoying high efficiency and good functional groups compatibility. Graphical Abstract An annulation reaction between N-methoxyindozamides and heterobicyclic alkenes was herein disclosed. The Rh-Ag-cocatalyzed system offered a direct approach towards various indolo[3,2-c]-1-azaanthraenes in high efficiency and good functional group tolerance. Successive treatment of acids gave different products of great importance.