Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes

Wang, Yong; Cao, Xinyi; Ji, Jingfei; Cui, Xiuling; Pi, Chao; Zhao, Leyao; Wu, Yangjie

doi:10.1016/j.cclet.2020.12.026

Cited by 14 publications

(2 citation statements)

References 61 publications

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“…In this context, devising alternative methods for vicinal diketone synthesis under transition metal-free, mild and sustainable conditions using simple substrates is highly urgent. Based on our interest in both visible light photocatalytic synthesis 17 and functionalization reactions resulting from π-bond cleavage, 18 we report herein a new method for vicinal diketone synthesis by organic dye (Eosin Y) triggered photocatalytic reactions of terminal alkynes and arene diazonium salts under mild room temperature conditions employing clean molecular oxygen 19 as the source of O-atoms (Scheme 1G-II). This is also the first photocatalytic synthesis of vicinal diketones under transition metal-free conditions.…”

Section: Introductionmentioning

confidence: 99%

Transition metal-free, photocatalytic arylation and dioxygenation for vicinal diketone synthesis using alkynes and arene diazonium salts

Zhao

Yin

et al. 2023

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Transition metal-free, photocatalytic arylation and dioxygenation for vicinal diketone synthesis using alkynes and arene diazonium salts

Zhao

Yin

et al. 2023

Org. Chem. Front.

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“…Tandem catalysis is a versatile tool for the synthesis of value-added products starting from inexpensive and readily available starting materials. − Notably, using alcohols as a coupling partner recently, several tandem protocols were developed. ,− In this context, the utilization of methanol as a transfer hydrogenation along with methylating agent is highly desirable.…”

Section: Introductionmentioning

confidence: 99%

(NNC)Ru(II) Complex Catalyzed Selective Functionalization of Ketones with Methanol: Understanding the Role of Ancillary Ligands

Ganguli,

Mandal,

Pradhan

et al. 2023

ACS Catal.

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Employing a single catalyst and substrate, the selective synthesis of all probable products upon varying the reaction conditions is uniquely challenging and exciting to explore. Utilizing methanol, cyclometalated (NNC)Ru(II) complex catalyzed selective transformation of a wide variety of ketones to the corresponding alcohols, β-methylated alcohols, and α-methylated ketones is disclosed. Notably, by changing the reaction parameters, the selective synthesis of all the probable products for the reactions of ketones with methanol was achieved. For these transformations, the role of different ancillary ligands (DMSO, CH 3 CN and PPh 3 ) coordinated to the Ru(II) center was investigated. This protocol was successfully applied for the functionalization of a few pharmaceutically important molecules and to sterically hindered α, α′-disubstituted and α, α′, α′′-trisubstituted ketones. Several control experiments, kinetic studies, Hammett studies, and DFT calculations were carried out to understand this catalytic process.

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Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

Zhao,

Pi,

et al. 2024

Adv Synth Catal

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Herein, a Rh‐catalyzed redox C7‐spiroannulation reaction of N‐benzo[d]imidazole indolines with maleimides has been reported, chemo‐ and regio‐ selectively providing a series of N‐benzo[d]imidazole indoline fused azaspirocycles in up to 92% yield. The synthetic utility is demonstrated by the synthesis of highly functionalized nitrogen‐containing spiropolycyclic skeletons, which could be extended to maleic esters and acrylates. The products could be purified through simple filtration. The recyclable Rh catalyst and scale‐up synthesis with as low as 0.5 mol% catalyst loading makes this protocol potential application in industrial. Moreover, the efficient post‐modification of pharmaceutical molecules demonstrates its practicability.

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Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes

Cited by 14 publications

References 61 publications

Transition metal-free, photocatalytic arylation and dioxygenation for vicinal diketone synthesis using alkynes and arene diazonium salts

Transition metal-free, photocatalytic arylation and dioxygenation for vicinal diketone synthesis using alkynes and arene diazonium salts

(NNC)Ru(II) Complex Catalyzed Selective Functionalization of Ketones with Methanol: Understanding the Role of Ancillary Ligands

Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

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