Kupferkatalysierte Azid‐Alkin‐Cycloadditionen: regioselektive Synthese von 1,4,5‐trisubstituierten 1,2,3‐Triazolen

Spiteri, Christian; Moses, John E.

doi:10.1002/ange.200905322

Cited by 60 publications

(4 citation statements)

References 32 publications

(11 reference statements)

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“…[2] Owing to its excellent fidelity and compatibility in a broad context, CuAAC has evolved into a powerful tool with wide applications in organic synthesis, molecular biology, and materials science. [3][4][5][6] In contrast to the widely successful use of terminal alkynes (including metal acetylides) in catalyzed AACs, [3] the corresponding reactions of internal alkynes for the synthesis of fully substituted 1,2,3-triazoles remain a challenge [7] owing to the increased energy barrier and difficulty in regiocontrol, particularly for intermolecular reactions. As a result, most intermolecular AACs of internal alkynes require high temperatures [8] and/or activated substrates, such as electrondeficient alkynes (e.g., haloalkynes) [9,10] or strained alkynes (e.g., cyclooctynes).…”

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confidence: 99%

Iridium‐Catalyzed Intermolecular Azide–Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions

2014

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An iridium-catalyzed azide-alkyne cycloaddition reaction (IrAAC) of electron-rich internal alkynes is described. It is the first efficient intermolecular AAC of internal thioalkynes. The reaction exhibits remarkable features, such as high efficiency and regioselectivity, mild reaction conditions, easy operation, and excellent compatibility with air and a broad spectrum of organic and aqueous solvents. It complements the well-known CuAAC and RuAAC click reactions.

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confidence: 99%

Iridium‐Catalyzed Intermolecular Azide–Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions

2014

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“…However, several groups developed alternative reaction protocols that allow the use of internal alkynes and especially 1-iodoalkynes [12] in 1,3dipolar cycloadditions with azides. [13] In addition, many transition metal azide complexes were applied in [3 + 2] cycloaddition reactions. [14] In 2007, Sedelmeier et al showed that reaction between aluminum azides and nitriles could be used to synthesize 5-substituted tetrazoles in good yield, the required temperature depending on the alkyne.…”

Section: Introductionmentioning

confidence: 99%

Bistriazoles Connected Through a B−B Bridge, Synthesized by Highly Selective Dipolar Cycloaddition Reactions of a Diazido‐diborane(4)

Vogler

Schöner

Kaifer

et al. 2022

Chemistry A European J

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In this work we report the first cycloaddition reactions between a diazido diborane(4) and terminal alkynes, providing unique access to bis-1,2,3-triazoles connected by a BÀ B bridge. The catalyst-free reactions are highly selective, yielding exclusively the thermodynamically disfavored bis-1,4triazoles. The reactions are enabled by the high thermal stability of the diazido-diborane [B(hpp)(N 3 )] 2 (hpp = 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-α]pyrimidinate). Due to the tetra-coordinate boron atoms in this reagent, the reactions are tolerant with respect to the introduction of Lewis-basic groups at the alkyne. The scope and limitations of the new reactions are discussed.

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“…Although elegant preparative methods for such motifs have been reported, synthetic methodologies allowing the rapid and regiospecific construction of 1,4,5-trisubstituted 1,2,3-triazoles tend to be extremely demanding. [8] While some direct protocols leading to 1,2,3-triazoles have been described, including tradition thermal [9] or metalfree [8c,d,f] [3+2] cycloadditions of linear alkynes or highly strained alkynes with azides, these reactions are often slow because of high activation energies (ca. 16-24 kcal mol À1 ), [10] and also produce a mixture of regioisomers (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Amine‐Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3‐Triazoles

Wang

Peng

Danence

et al. 2012

Chemistry A European J

165

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An enamine-catalyzed strategy has been utilized to fully promote the Huisgen [3+2] cycloaddition with a broad spectrum of carbonyl compounds and azides, thereby permitting the efficient assembly of a vast pool of highly substituted 1,2,3-triazoles. In particular, the employment of commonly used and commercially available carbonyl compounds has resulted in the introduction of a diverse set of functional groups, such as alkyl, aryl, nitrile, ester, and ketone groups, at the 1-, 4-, or 5-positions of the 1,2,3-triazole scaffold. This approach might be manipulated to access more useful and sophisticated heterocyclic compounds. Most significantly, the reaction process exhibits complete regioselectivity, with the formation of only one regioisomer.

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Kupferkatalysierte Azid‐Alkin‐Cycloadditionen: regioselektive Synthese von 1,4,5‐trisubstituierten 1,2,3‐Triazolen

Cited by 60 publications

References 32 publications

Iridium‐Catalyzed Intermolecular Azide–Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions

Iridium‐Catalyzed Intermolecular Azide–Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions

Bistriazoles Connected Through a B−B Bridge, Synthesized by Highly Selective Dipolar Cycloaddition Reactions of a Diazido‐diborane(4)

Amine‐Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3‐Triazoles

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