Photocatalytic coupling of electron-deficient alkenes using oxalic acid as a traceless linchpin

Wu, Zugen; Wu, Mingyue; Zhu, Kun; Wu, Jie; Lü, Yixin

doi:10.1016/j.chempr.2022.12.013

Cited by 26 publications

(16 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, Lu's group developed a reductive alkene crosscoupling reaction, providing a straightforward way to construct C−C bonds from readily available alkene feedstocks with oxalic acid as a traceless linchpin (Scheme 41). 59 This one-pot reaction was enabled by a dual-photocatalyst system, providing a mild and easy pathway for the generation of a CO 2…”

Section: Photopromoted Synthesis Of Carboxylic Acids and Estersmentioning

confidence: 99%

“…Recently, Lu’s group developed a reductive alkene cross-coupling reaction, providing a straightforward way to construct C–C bonds from readily available alkene feedstocks with oxalic acid as a traceless linchpin (Scheme ). This one-pot reaction was enabled by a dual-photocatalyst system, providing a mild and easy pathway for the generation of a CO 2 •– from oxalic acid, which circumvented the addition of a HAT catalyst or strong reductive photocatalyst. Base on mechanistic studies, a plausible mechanism is illustrated in Scheme .…”

Section: Co2 •– As Reactant To Access Carboxylic Acids and Estersmentioning

confidence: 99%

“…In the same year, Nam's group demonstrated the same reaction with water as the Scheme 41. Reductive Alkene Cross-Coupling with Oxalic Acid as a Traceless Linchpin59…”

mentioning

confidence: 99%

See 2 more Smart Citations

Recent Advances in Reactions Involving Carbon Dioxide Radical Anion

Xiao,

Zhang,

2023

ACS Catal.

Self Cite

View full text Add to dashboard Cite

Section: Photopromoted Synthesis Of Carboxylic Acids and Estersmentioning

confidence: 99%

Section: Co2 •– As Reactant To Access Carboxylic Acids and Estersmentioning

confidence: 99%

See 1 more Smart Citation

Recent Advances in Reactions Involving Carbon Dioxide Radical Anion

Xiao,

Zhang,

2023

ACS Catal.

Self Cite

View full text Add to dashboard Cite

“…The recent advances in methodologies for the generation of radical species, such as photoredox catalysis and electrocatalysis, have made these conditions milder and more practical. Despite these breakthroughs, the linchpin coupling strategy based on radical-mediated C–C bond formations has been less explored …”

Section: Introductionmentioning

confidence: 99%

Bidirectional Elongation Strategy Using Ambiphilic Radical Linchpin for Modular Access to 1,4-Dicarbonyls via Sequential Photocatalysis

2023

View full text Add to dashboard Cite

Organic molecules that can be connected to multiple substrates by sequential C–C bond formations can be utilized as linchpins in multicomponent processes. While they are useful for rapidly increasing molecular complexity, most of the reported linchpin coupling methods rely on the use of organometallic species as strong carbon nucleophiles to form C–C bonds, which narrows the functional group compatibility. Here, we describe a metal-free, radical-mediated coupling approach using a formyl-stabilized phosphonium ylide as a multifunctional linchpin under visible-light photoredox conditions. The present method uses the ambiphilic character of the phosphonium ylide, which serves as both a nucleophilic and an electrophilic carbon-centered radical source. The stepwise and controllable generation of these radical intermediates allows sequential photocatalysis involving two mechanistically distinct radical additions, both of which are initiated by the same photocatalyst in one pot with high functional group tolerance. The methodology enables a bidirectional assembly of the linchpin with two electronically differentiated alkene fragments and thus offers rapid and modular access to 1,4-dicarbonyl compounds as versatile synthetic intermediates.

show abstract

“…If successful, this protocol would open an interesting avenue for synthesizing structurally divergent diuorinated hydrocarbons, with ClCF 2 SO 2 Na serving as a practical "linchpin". [42][43][44][45][46][47][48] While the "linchpin" strategy has been explored in recent years to link two molecular skeletons through linkers such as alkyne, alkene, and sulfone groups, its application in organouorine chemistry remains underdeveloped. [49][50][51] Herein, we collaborated with colleagues from Pzer to prepare ClCF 2 SO 2 Na in kilogram-scale.…”

Section: Introductionmentioning

confidence: 99%