Synthesis and reactivity of 1-sulfonylcyclooctatriazoles

Williams, Matthew B.; Wells, Ruaraidh J; Boyer, Alistair

doi:10.1039/d2cc03648g

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Table 1 Optimisation Overview A1

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2023

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Cited by 2 publications

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“…The highest yields in the reaction were observed between zinc acetylides and electron-poor azides (Scheme 3b ). It is recognised that alkyl azides are significantly more electron-rich than their aromatic counterparts, 24d 29 which explains the slow reaction and low yield of benzyl azide. Therefore, a third method was developed using a more reactive metal.…”

Section: Table 1 Optimisation Overview Amentioning

confidence: 99%

Exploiting 1,1-Dibromoalkenes as Direct Precursors to 5-Substituted 1,2,3-Triazoles

Boyer¹,

Williams²,

Martin³

et al. 2023

Synthesis

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Abstract1,1-Dibromoalkenes can be used as direct precursors to three classes of 5-substituted 1,2,3-triazoles. Three different approaches to 1,2,3-triazole products were developed, linked to the N1-substituent. Treatment of 1,1-dibromoalkenes with n-butyllithium and reaction with a sulfonyl azide gave 5-substituted 1-sulfonyl-1,2,3-triazoles. The use of lithium base followed by transmetalation to zinc and reaction with aryl azides allowed access to 1-aryl-1,2,3-triazoles. Finally, the use of EtMgBr as base and reaction with an alkyl azide formed 1-alkyl-1,2,3-triazoles.

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Section: Table 1 Optimisation Overview Amentioning

confidence: 99%