Direct Electrophilic C−H Alkynylation of Unprotected 2‐Vinylanilines

Caspers, Lucien D.; Finkbeiner, Peter; Nachtsheim, Boris J.

doi:10.1002/chem.201606026

Cited by 35 publications

(10 citation statements)

References 104 publications

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“…In line with this result, the same group has explored the directing ability of amine groups and presented the C( sp 2 )−H alkynylation of unprotected aromatic amines, 152 [78] . The protocol required Ir(III) catalyst and alkynylbenziodoxolones as electrophilic alkyne transfer reagents.…”

Section: Transition‐metal‐catalyzed Olefinic C(sp2)−h Alkynylationmentioning

confidence: 95%

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

et al. 2021

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Alkynylation reactions are one of the most sought‐after synthetic methodologies due to the versatility of C−C triple bond diversifications. Sonogashira coupling was widely used for the synthesis of alkynylated molecules; however, this methodology requires the use of previously halogenated substrates, which is a major drawback. To overcome this issue, a complimentary method, transition‐metal‐catalyzed C−H alkynylation, was emerged as an alternative tool in the recent years. Though the initial reports required the use of either specific directing groups or strong alkynylating agents for effective functionalization, recent studies indicate that transition‐metal‐catalyzed site selective alkynylations can be carried out using mild and readily available alkynylating agents under moderate reaction conditions. In this review, we explain the transition metal cataluyzed site selective alkynylation both C(sp2)−H and C(sp3)−H bonds by emphasizing to the reaction mechanism.

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Section: Transition‐metal‐catalyzed Olefinic C(sp2)−h Alkynylationmentioning

confidence: 95%

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

et al. 2021

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“…Compared to phenolates, anilines are much more Lewis‐basic, in particular under neutral conditions, and therefore even more challenging DGs in TM‐catalyzed transformations due to destructive side pathways such as irreversible catalyst deactivation. Nevertheless, a selective alkynylation of o ‐vinylanilines 116 could be achieved (Scheme ) . With an Ir III ‐catalyst and 1 a the desired enynes 117 were obtained in good yields and stereoselectivities.…”

Section: Directed C−h Alkynylationmentioning

confidence: 99%

Directing‐Group‐mediated C−H‐Alkynylations

Caspers

Nachtsheim

2018

Chemistry An Asian Journal

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C-C triple bonds are amongst the most versatile functional groups in synthetic chemistry. Complementary to the Sonogashira coupling the direct metal-catalyzed alkynylation of C-H bonds has emerged as a highly promising approach in recent years. To guarantee a high regioselectivity suitable directing groups (DGs) are necessary to guide the transition metal (TM) into the right place. In this Focus Review we present the current developments in DG-mediated C(sp )-H and C(sp )-H modifications with terminal alkynes under oxidative conditions and with electrophilic alkynylation reagents. We will discuss further modifications of the alkyne, in particular subsequent cyclizations to carbo- and heterocycles and modifications of the DG in the presence of the alkyne.

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“…In this regard, there are several procedures in the literature for the preparation of these N ‐containing polycycles, mainly involving cyclization reactions [12] . Although most of these methods are very effective, and despite the significant recent advances, some limitations are still present, which includes the use of transition metals, such as Fe, [12c] Cu, [12d–f] or Pd, [12g–i] and require various reaction steps and complex starting materials, which are challenging to prepare and environmentally incompatible [12j–l] …”

Section: Introductionmentioning

confidence: 99%

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

et al. 2020

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In this work, a one-pot sequential organocatalytic method for the synthesis of fused [1,2,3]triazolo [1,5-a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3 + 2]-cycloaddition occurs between 1,3-dicarbonyl compounds and o-carbonyl-substituted phenylazide compounds, for the formation of the 1,2,3-triazole intermediates. Subsequently, an intramolecular condensation reaction generates the fused quinoline ring by the new CÀ C bond formation, giving the products in yields ranging from moderate to excellent. All the reactions were performed using 20 mol% of 1,8diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst in the presence of DMSO as solvent at 120°C for 24 h and tolerate a range of 1,3-dicarbonyl compounds, such as β-keto esters and 1,3-diketones, and o-formyl, o-acetyl or o-benzoyl substituted phenylazide compounds.

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Direct Electrophilic C−H Alkynylation of Unprotected 2‐Vinylanilines

Cited by 35 publications

References 104 publications

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Directing‐Group‐mediated C−H‐Alkynylations

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

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