Rhodium-Catalyzed Regiodivergent [3 + 2] and [5 + 2] Cycloadditions of Quinolinium Ylides with Alkynes

He, Min; Chen, Nuan; Wang, Jian; Peng, Shiyong

doi:10.1021/acs.orglett.9b01765

Cited by 32 publications

(20 citation statements)

References 72 publications

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“…In 2019, Peng et al reported a rhodium-catalyzed regiodivergent [3 + 2]-and [5 + 2]-cycloadditions of quinolinium ylides with alkynes (Scheme 8). [20] In this work, different types of donor-acceptor diazo compounds exhibited distinct reactivity and outcomes. Only the diazoesters (20, A=CO 2 R) produced the [3 + 2]-cycloaddition adducts, followed by an unusual 1,3-ester migration process to give the tricyclic product 22.…”

Section: Rh-catalyzed [3 + 2]-cycloadditionmentioning

confidence: 85%

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Dong

2020

Asian J Org Chem

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Pyridinium ylide is a versatile building block in synthetic organic chemistry, especially in the synthesis of N‐heterocycles. In this minireview, we have summarized the advances of [3+2]‐cycloaddition of catalytically generated pyridinium ylide for the synthesis of indolizines (since 1970s). Accordingly, the ylide discussed in this article is generated in situ from carbene precursors and N‐heteroarenes under catalytic conditions, including photocatalysis/thermocatalysis, and metal‐catalysis. The metal‐catalyzed version is the main focus, which is classified and summarized based on the type of dipolarophiles, alkyne and alkene, each class is further subdivided according to the metal catalysts used in these reactions. The analogous [3+2]‐cycloaddition of vinyl metal carbene with pyridines, the formation of pyridinium ylide with other type of carbene precursors or with different N‐heteroarenes, have been also included herein separately.

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Section: Rh-catalyzed [3 + 2]-cycloadditionmentioning

confidence: 85%

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Dong

2020

Asian J Org Chem

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“…In 2019, rhodium-catalyzed multicomponent and regiodivergent cycloadditions of quinolines, donor-acceptor diazo compounds and electron-deficient alkynes was investigated by Peng and co-workers. 43…”

Section: Reaction With Alkynes/arynesmentioning

confidence: 99%

Recent Applications of Quinolinium Salts in the Synthesis of Annulated Heterocycles

Das¹

2022

SynOpen

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Quinoline derivatives are frequently found in natural products and biologically active compounds, however, construction of quinoline fused polyheterocycles is the challenging goal in synthetic organic chemistry. In this regard, quinolinium salts meet the demand to a great level, as they can be synthesized readily and employed effectively for the rapid construction of condensed heterocyclic core. The present review focuses on recent (2015-2021) applications of different quinolinium salts that react with suitable partners to access diverse annulated products. Most of the reactions discussed here involve easily available starting materials, operationally simple, high atom efficiency and environmentally benign. Mechanistic aspects of representative transformations have also been highlighted for better understanding of reaction pathway.

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“…Peng and co-workers described a rhodium-catalyzed multicomponent cycloaddition of a quinoline 55, a diazo compound 125, and an electron-deficient alkyne 8, which resulted in a [3+2] indolizine derivative and a [5+2] 1,4-oxazepine compound, respectively (Scheme 27). 89 Additionally, quinolinium ylides derived from different types of donor−acceptor diazo compounds exhibit distinct selectivity and reactivity for the reactions. The [3+2] cycloadditions involve an unusual meta-assisted 1,3-ester migration process,.…”

Section: Scheme 22mentioning

confidence: 99%

Sequential and direct multicomponent reaction (MCR)-based dearomatization strategies

et al. 2020

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Rhodium-Catalyzed Regiodivergent [3 + 2] and [5 + 2] Cycloadditions of Quinolinium Ylides with Alkynes

Cited by 32 publications

References 72 publications

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Recent Applications of Quinolinium Salts in the Synthesis of Annulated Heterocycles

Sequential and direct multicomponent reaction (MCR)-based dearomatization strategies

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