Azido-type-selective triazole formation by iridium-catalyzed cycloaddition with thioalkynes

Sugiyama, Kazuya; Sakata, Yuki; Niwa, Takashi; Yoshida, Suguru; Hosoya, Takamitsu

doi:10.1039/d2cc01739c

Cited by 7 publications

(1 citation statement)

References 34 publications

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“…Recent findings have shown a preference for benzyl azide in IrAAC reactions compared to phenyl azide. 31 In order to leverage this preference in our synthetic approach, we synthesized three diazido monomers ( A1 to A3 ), each featuring these two types of azido groups, and probed the chemoselectivity of IrAAC in their respective reaction with thioalkyne T1 . As illustrated in Scheme 2A, the IrAAC reactions of both p -(azidomethyl)phenyl azide ( A1 ) and m -(azidomethyl)phenyl azide ( A2 ) were highly efficient, yielding the desired monotriazole T-A with high selectivity.…”

Section: Resultsmentioning

confidence: 99%

Exploiting chemoselectivity for discrete oligomer synthesis through sequential IrAAC and CuAAC reactions

Song,

Zhang,

Ding

2024

Polym. Chem.

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Section: Resultsmentioning

confidence: 99%

Exploiting chemoselectivity for discrete oligomer synthesis through sequential IrAAC and CuAAC reactions

Song,

Zhang,

Ding

2024

Polym. Chem.

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Five-membered ring systems: with more than one N atom

Yet

2023

Progress in Heterocyclic Chemistry

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Process-Divergent Syntheses of 4- and 5-Sulfur-Functionalized 1,2,3-Triazoles via Copper-Catalyzed Azide–Alkyne Cycloadditions of 1-Phosphinyl-2-sulfanylethynes

et al. 2023

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4-Sulfanyl-substituted 1,2,3-triazoles were provided regioselectively with good yields and broad scope via consecutive t-BuOK-promoted dephosphinylation of 1-phosphinyl-2-sulfanylethynes and copper-catalyzed azide–alkyne cycloadditions (CuAAC) with alkyl azides. Unsymmetrically substituted ditriazoles were successfully obtained using a tandem dephosphinylative CuAAC protocol with diazides. Direct CuAAC of the 1-phosphinyl-2-sulfanylethynes with azides afforded regioisomeric mixtures of 4-phosphinyl-5-sulfanyl- and 5-phosphinyl-4-sulfanyl-1,2,3-triazoles that were easily separable from one another. When the phosphinyl- and sulfanyl-substituted triazoles were treated with t-BuOK, the dephosphination proceeded smoothly, yielding the corresponding 5- and 4-sulfanyltriazoles, respectively. 5-(1-Aryl-1-hydroxymethyl)-4-sulfanyltriazoles were synthesized by stepwise treatment of 5-phosphinyl-4-sulfanyltriazole with MeMgBr and arylaldehydes. Additionally, Ph2P(O) and RS groups in the triazoles were easily converted to Ph2P and RSO2 by PhSiH3-reduction and m-CPBA-oxidation, respectively. Following the dephosphinylative CuAAC of 1-phosphinyl-2-(4-t-butylphenylsulfanyl)ethyne with aryl azides and m-CPBA-oxidation, potent antagonists of pregnane X receptor LC-58 and LC-59 were successfully produced.

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Azido-type-selective triazole formation by iridium-catalyzed cycloaddition with thioalkynes

Abstract: Iridium-catalyzed azide–thioalkyne cycloaddition was found to be effective for the azido-type-selective reaction of various multiazido compounds, enabling facile synthesis of multitriazole compounds in short steps.

Cited by 7 publications

References 34 publications

Exploiting chemoselectivity for discrete oligomer synthesis through sequential IrAAC and CuAAC reactions

Exploiting chemoselectivity for discrete oligomer synthesis through sequential IrAAC and CuAAC reactions

Five-membered ring systems: with more than one N atom

Process-Divergent Syntheses of 4- and 5-Sulfur-Functionalized 1,2,3-Triazoles via Copper-Catalyzed Azide–Alkyne Cycloadditions of 1-Phosphinyl-2-sulfanylethynes

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