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Synthesis 2023; 55(22): 3862-3874
DOI: 10.1055/s-0042-1751464
DOI: 10.1055/s-0042-1751464
paper
Exploiting 1,1-Dibromoalkenes as Direct Precursors to 5-Substituted 1,2,3-Triazoles
Alistair Boyer was a Royal Society /TATA University Research Fellow. Matthew B. Williams was funded by a Royal Society PhD studentship. Steffen Wiedmann was a Deutscher Akademischer Austauschdienst (DAAD) RISE exchange student.
Abstract
1,1-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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751464.
- Supporting Information
Publication History
Received: 29 March 2023
Accepted after revision: 26 May 2023
Article published online:
27 June 2023
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