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Synlett
DOI: 10.1055/a-2705-9082
Letter

A tandem aldol/desilylation/CuAAC sequence of difluoroenoxysilanes and silyl-α-ketoalkynes to α-fluoroketone α-1,2,3 triazole tertiary alcohol

ZhiChao Liu
1   School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, China (Ringgold ID: RIN70586)
,
Tao Wang
2   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China (Ringgold ID: RIN12655)
,
Shengchao Yang
1   School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, China (Ringgold ID: RIN70586)
,
Jian Zhou
3   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China
,
Jin-Sheng Yu
2   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China (Ringgold ID: RIN12655)
› Institutsangaben
Gefördert durch: Technology Innovation Project of Shanghai Municipal Agricultural Committee HNK(T2023302)
Gefördert durch: National Natural Science Foundation of China 22171087
Gefördert durch: Innovation Program of Shanghai Municipal Education Commission 2023ZKZD37
Gefördert durch: other fund 2023AA004,2023B01019,2024AB055
Gefördert durch: the Ministry of Education (PCSIRT) and the Fundamental Research Funds for the Central Universities 123, 457, 1233
› Weitere Informationen
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A one-pot tandem aldol/desilylation/CuAAC sequence is developed, allowing facile synthesis of tertiary alcohols featuring an α-difluoroketone moiety and a 1,2,3-triazole at the α position in moderate to good yields, with an operationally friendly manner. While Bi(OTf)3 was the optimal catalyst for the Mukaiyama-aldol reaction of silyl-α-ketoalkynes and difluoroenoxysilanes, CuCl was found to efficiently mediate the alkyne-azide cycloaddition.



Publikationsverlauf

Eingereicht: 10. Juli 2025

Angenommen nach Revision: 02. September 2025

Accepted Manuscript online:
19. September 2025

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