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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Direct Synthesis of alpha-Fluoro-alpha-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach

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Author(s):
Day, David Philip [1] ; Mora Vargas, Jorge Andres [1] ; Bender Burtoloso, Antonio Carlos [1]
Total Authors: 3
Affiliation:
[1] Univ Sao Paulo, Sao Carlos Inst Chem, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Organic Chemistry; v. 86, n. 17, p. 12427-12435, SEP 3 2021.
Web of Science Citations: 0
Abstract

The work reported herein showcases a new route to access alpha-fluoro-alpha-triazol-1-yl ketones from sulfoxonium ylides via aazido-alpha-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N-3(-), followed by a subsequent CuAAC reaction with arylacetylenes to install a 1,4-triazolo moiety. The approach allows for modification to both the sulfoxonium ylide and arylacetylene reactants. Fifteen examples have been reported, with yields ranging between 22% and 75%. (AU)

FAPESP's process: 20/07147-0 - Enantioselective alpha-heterofunctionalization of carbonyl compounds using sulfoxonium ylides
Grantee:Antonio Carlos Bender Burtoloso
Support Opportunities: Regular Research Grants
FAPESP's process: 19/05002-8 - Exploration of Enantioselective Transformations of Diazoketones and Sulfoxonium Ylides
Grantee:David Philip Day
Support Opportunities: Scholarships in Brazil - Post-Doctoral