Ruthenium (II)‐Catalyzed Oxidant‐Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines

Shi, Xinxia; Wang, Rongchao; Zeng, Xiaofei; Zhang, Yilan; Hu, Huiling; Xie, Changde; Wang, Min

doi:10.1002/adsc.201800844

Cited by 76 publications

(38 citation statements)

References 73 publications

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“…It was generally proposed that the cyclic product was formed by the first generation of an acylmethylation intermediate in similar cascade reactions. (Chen et al, 2018;Hu et al, 2018aHu et al, ,b, 2019Liang et al, 2018;Shi et al, 2018;Xiao et al, 2018;Xie et al, 2018bXie et al, , 2019Xie H. et al, 2018;Xu et al, 2018;Zhou et al, 2018;Cai et al, 2019;Chen P. et al, 2019;Cui et al, 2019;Huang et al, 2019;Lai et al, 2019;Liu et al, 2019;Luo et al, 2019;Lv et al, 2019;Nie et al, 2019;Shen et al, 2019;Wu C. et al, 2019;Zhang et al, 2019Zhang et al, , 2020Wu et al, 2020). Further transformations from IM6 were explored theoretically to confirm whether the acylmethylation intermediate (IM8) is key in the formation of 2a (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study

Zhang

Teng

et al. 2020

Front. Chem.

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A mild ruthenium(II)-catalyzed homocoupling of α-carbonyl sulfoxonium ylides was developed and the detailed mechanism was understood based on DFT calculations in the current report. The catalytic system utilizes the α-carbonyl sulfoxonium ylide as both the directing group for ortho-sp 2 C-H activation and the acylmethylating reagent for CC coupling. Various substituents are compatible in the transformation and a variety of isocoumarin derivatives were synthesized at room temperature without any protection. The theoretical results disclosed that the full catalytic cycle contains eight elementary steps, and in all the cationic Ru(II) monomer is involved as the catalytic active species. The acid additive is responsible for protonation of the ylide carbon prior to the intramolecular nucleophilic addition and CC bond cleavage. Interestingly, the intermediacy of free acylmethylation intermediate or its enol isomer is not necessary for the transformation.

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Section: Resultsmentioning

confidence: 99%

Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study

Zhang

Teng

et al. 2020

Front. Chem.

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“…Various functional groups were well tolerated under developed reaction conditions to obtain the desired product (Scheme 256). [263] A plausible reaction mechanism was drawn based on experimental results and literature reports (Scheme 257). [264][265] In 2019, Deshmukh and Bhanage reported a Rucatalyzed annulation of N-Cbz hydrazines 418 via CÀ H/NÀ N bond activation towards the synthesis of isoquinoline 74.…”

Section: Ru-catalyzed Isoquinoline Synthesismentioning

confidence: 99%

Section: Synthesis Of Isoquinoline Derivativesmentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.

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“…In 2018, Wang et al. reported Ru‐catalyzed synthesis of isoquinolines from sulfoxonium ylides and benzimidates via C−H functionalization/annulation cascade process (Scheme b) . Likewise, Zeng et al.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium Catalyzed C−H Acylmethylation of N‐Arylphthalazine‐1,4‐diones with α‐Carbonyl Sulfoxonium Ylides: Highway to Diversely Functionalized Phthalazino‐fused Cinnolines

Karishma

Agarwal

Laha

et al. 2019

Chemistry An Asian Journal

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A direct ortho‐Csp2‐H acylmethylation of 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with α‐carbonyl sulfoxonium ylides is achieved through a RuII‐catalyzed C−H bond activation process. The protocol featured high functional group tolerance on the two substrates, including aryl‐, heteroaryl‐, and alkyl‐substituted α‐carbonyl sulfoxonium ylides. Thereafter, 2‐(ortho‐acylmethylaryl)‐2,3‐dihydrophthalazine‐1,4‐diones were used as potential starting materials for the expeditious synthesis of 6‐arylphthalazino[2,3‐a]cinnoline‐8,13‐diones and 5‐acyl‐5,6‐dihydrophthalazino[2,3‐a]cinnoline‐8,13‐diones under Lawesson's reagent and BF3⋅OEt2 mediated conditions, respectively. Of these, the BF3⋅OEt2‐mediated cyclization proceeded in DMSO as a solvent and a methylene source via dual C−C and C−N bond formations.

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Ruthenium (II)‐Catalyzed Oxidant‐Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines

Cited by 76 publications

References 73 publications

Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study

Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Ruthenium Catalyzed C−H Acylmethylation of N‐Arylphthalazine‐1,4‐diones with α‐Carbonyl Sulfoxonium Ylides: Highway to Diversely Functionalized Phthalazino‐fused Cinnolines

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