A Tandem Aldol/Desilylation/CuAAC Sequence of Difluoroenoxysilanes and Silyl-α-ketoalkynes to α-Fluoroketone α-1,2,3 Triazole Tertiary Alcohol

Zhi Chao Liu; Tao Wang; Shengchao Yang; Jian Zhou; Jin Sheng Yu

doi:10.1055/a-2705-9082

A Tandem Aldol/Desilylation/CuAAC Sequence of Difluoroenoxysilanes and Silyl-α-ketoalkynes to α-Fluoroketone α-1,2,3 Triazole Tertiary Alcohol

Zhi Chao Liu, Tao Wang^*, Shengchao Yang, Jian Zhou, Jin Sheng Yu

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

Abstract

A one-pot tandem aldol/desilylation/CuAAC sequence is developed, allowing the 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) ₃was the optimal catalyst for the Mukaiyama-aldol reaction of silyl-α-ketoalkynes and difluoroenoxysilanes, CuCl was found to efficiently mediate the alkyne-azide cycloaddition.

Original language	English
Journal	Synlett
DOIs	https://doi.org/10.1055/a-2705-9082
State	Accepted/In press - 2025

Keywords

Aldol/desilylation/CuAAC reaction
Difluoroenoxysilanes
Silyl-α-ketoalkynes
α-Fluoroketone α-1,2,3 triazole tertiary alcohol

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10.1055/a-2705-9082

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title = "A Tandem Aldol/Desilylation/CuAAC Sequence of Difluoroenoxysilanes and Silyl-α-ketoalkynes to α-Fluoroketone α-1,2,3 Triazole Tertiary Alcohol",

abstract = "A one-pot tandem aldol/desilylation/CuAAC sequence is developed, allowing the 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) 3was the optimal catalyst for the Mukaiyama-aldol reaction of silyl-α-ketoalkynes and difluoroenoxysilanes, CuCl was found to efficiently mediate the alkyne-azide cycloaddition.",

keywords = "Aldol/desilylation/CuAAC reaction, Difluoroenoxysilanes, Silyl-α-ketoalkynes, α-Fluoroketone α-1,2,3 triazole tertiary alcohol",

author = "Liu, \{Zhi Chao\} and Tao Wang and Shengchao Yang and Jian Zhou and Yu, \{Jin Sheng\}",

year = "2025",

doi = "10.1055/a-2705-9082",

language = "英语",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - A Tandem Aldol/Desilylation/CuAAC Sequence of Difluoroenoxysilanes and Silyl-α-ketoalkynes to α-Fluoroketone α-1,2,3 Triazole Tertiary Alcohol

AU - Liu, Zhi Chao

AU - Wang, Tao

AU - Yang, Shengchao

AU - Zhou, Jian

AU - Yu, Jin Sheng

PY - 2025

Y1 - 2025

N2 - A one-pot tandem aldol/desilylation/CuAAC sequence is developed, allowing the 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) 3was the optimal catalyst for the Mukaiyama-aldol reaction of silyl-α-ketoalkynes and difluoroenoxysilanes, CuCl was found to efficiently mediate the alkyne-azide cycloaddition.

AB - A one-pot tandem aldol/desilylation/CuAAC sequence is developed, allowing the 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) 3was the optimal catalyst for the Mukaiyama-aldol reaction of silyl-α-ketoalkynes and difluoroenoxysilanes, CuCl was found to efficiently mediate the alkyne-azide cycloaddition.

KW - Aldol/desilylation/CuAAC reaction

KW - Difluoroenoxysilanes

KW - Silyl-α-ketoalkynes

KW - α-Fluoroketone α-1,2,3 triazole tertiary alcohol

UR - https://www.scopus.com/pages/publications/105021050805

U2 - 10.1055/a-2705-9082

DO - 10.1055/a-2705-9082

M3 - 文章

AN - SCOPUS:105021050805

SN - 0936-5214

JO - Synlett

JF - Synlett

ER -

A Tandem Aldol/Desilylation/CuAAC Sequence of Difluoroenoxysilanes and Silyl-α-ketoalkynes to α-Fluoroketone α-1,2,3 Triazole Tertiary Alcohol

Abstract

Keywords

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