Ruthenium Catalyzed Divergent Alkylation and Olefination of Methyl 1,3,5‐Triazines with Alcohols

Su, C. J.; Zeng, Ming; Zhang, Chen; Cui, Dongmei

doi:10.1002/ejoc.202000781

Cited by 11 publications

(4 citation statements)

References 70 publications

(9 reference statements)

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“…The initial compound 1 was prepared as referred to in our previous work [38,39,45]. Sodium (2.5 eq) was added to anhydrous MeOH at 0 • C until the sodium was completely consumed.…”

Section: General Procedures For the Synthesis Ofmentioning

confidence: 99%

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

et al. 2023

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1,3,5 triazines, especially indole functionalized triazine derivatives, exhibit excellent activities, such as anti-tumor, antibacterial, and anti-inflammatory activities. Traditional methods for the synthesis of N-(2-triazine) indoles suffer from unstable materials and tedious operations. Transition-metal-catalyzed C-C/C-N coupling provides a powerful protocol for the synthesis of indoles by the C-H activation strategy. Here, we report the efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation from alkynes and various substituted triazine derivatives in a moderate to good yield, and all of the N-(2-triazine) indoles were characterized by 1H NMR, 13C NMR, and HRMS. This protocol can apply to the gram-scale synthesis of the N-(2-triazine) indole in a moderate yield. Moreover, the reaction is proposed to be performed via a six-membered ruthenacycle (II) intermediate, which suggests that the triazine ring could offer chelation assistance for the formation of N-(2-triazine) indoles.

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“…The initial compound 1 was prepared as referred to in our previous work [38,39,45]. Sodium (2.5 eq) was added to anhydrous MeOH at 0 • C until the sodium was completely consumed.…”

Section: General Procedures For the Synthesis Ofmentioning

confidence: 99%

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

et al. 2023

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“…In one of the latest articles in this area, Cui et al . disclosed a simple, facile, and high atom economical Ru‐catalyzed divergent alkylation as well as olefination of methyl 1,3,5‐triazines (Scheme 25), [33] which are bio‐active molecules and exhibit several antibacterial, anti‐HSV‐1, anticancer, and anti‐HIV properties. They have achieved the selectivity either towards alkylation or alkenylation by sensibly choosing the Ru‐catalyst; [Ru(PPh 3 ) 3 Cl 2 ] yields the alkylated 1,3,5‐triazine derivatives, while RuCl 3 provides the corresponding olefinated 1,3,5‐triazine derivatives.…”

Section: C−c Alk(en)ylation Of Methyl Heteroarenesmentioning

confidence: 99%

Atom‐Economic Alk(en)ylations of Esters, Amides, and Methyl Heteroarenes Utilizing Alcohols Following Dehydrogenative Strategies

et al. 2021

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Owing to the atom‐economic and greener nature, borrowing hydrogen (BH) and acceptorless dehydrogenative coupling (ADC) processes have drawn significant attentions of the researchers across the globe and thus, these strategies have been extensively utilized in synthetic chemistry to access various challenging and valuable compounds. During the last decade, significant progress has been witnessed in the utilization of these protocols involving alkylation of amides/esters/N‐heteroarenes by replacing the traditionally utilized mutagenic reagents as alkyl source with the sustainable biomass derived alcohols under BH/ADC process. This progress includes mainly the transition metal based catalytic systems although a few metal‐free protocols are reported. In this minireview, the advancement from 2010 until September 2020 in accessing C‐alk(en)ylated compounds from the unactivated amides/esters/N‐heteroarenes utilizing alcohols via BH/ADC strategy is highlighted. Additionally, a few reports on aldehydes instead of alcohols as coupling partners are also discussed.

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“…4 This strategy has been successfully applied for the switchable synthesis of amine/imine, alcohol/ketone, and alkylated/olefinic nitriles by controlling the selectivity between the BH and ADC processes. 5 However, the switchable synthesis of alkylated diamines/benzimidazole derivatives from the coupling of 1,2-phenylenediamine with alcohols through BH or ADC using a single system is challenging due to the formation of four different possible products (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Control over borrowing hydrogen and acceptorless dehydrogenative coupling process for the Co(iii)–NHC catalysed chemoselective alkylation and cyclisation of 1,2-phenylenediamine with alcohols

Siddique,

Boity,

Rit

2023

Catal. Sci. Technol.

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Ruthenium Catalyzed Divergent Alkylation and Olefination of Methyl 1,3,5‐Triazines with Alcohols

Cited by 11 publications

References 70 publications

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

Atom‐Economic Alk(en)ylations of Esters, Amides, and Methyl Heteroarenes Utilizing Alcohols Following Dehydrogenative Strategies

Control over borrowing hydrogen and acceptorless dehydrogenative coupling process for the Co(iii)–NHC catalysed chemoselective alkylation and cyclisation of 1,2-phenylenediamine with alcohols

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