One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride

严兆华,; 金红爱,; 余信权,; 王汪阳,; 田伟生,

doi:10.6023/cjoc201608008

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References 6 publications

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“…最近我们还报道了全氟烷基磺酰氟应用于活化二苯基膦氧和醇之间的 Arthen-Todd-like 反应生成了相应的膦酸酯化合物 [11] . 前文中我们已经报道了全氟烷基磺酰氟可以应用于活化苄醇化合物并和 1,3-二羰基化合物之间发生一步 C-或 O-苄基化反应 [12] . 作为课题研究的深入, 我们继续报道在碱性介质中, 全氟烷基磺酰 [12] , 考察了 1,3-二羰基化合物底物的适用范围.…”

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One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

严兆华¹,

王彦梅²,

金红爱³

et al. 2019

Chin. J. Org. Chem.

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O-Acylation of 1,3-dicarbonyl compounds provides enol esters which act as precursors for the synthesis of chiral alcohols, natural products, heterocycles and functional materials. Perfluoroalkanosulfonyl fluoride (R f SO 2 F) is a class of excellent hydroxyl-activating reagent, and has been extensively developed and used in the formation of C-F, CO , C-N and C-S bonds in organic synthesis. In this work one-step O-acylation of 1,3-dicarbonyl compounds (1,3-diketones and β-ketonic esters) with carboxylic acids activated by R f SO 2 F in alkaline media was disclosed, and the corresponding O-acylation products (enol esters) were generated in moderate to good yields. The optimized reaction conditions are as follows: 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) as base, CH 2 Cl 2 as solvent, n-C 4 F 9 SO 2 F as activating reagent, room temperature for 30 min and the molar ratio of n(1,3-dicarbonyls)∶n(RCOOH)∶n(R f SO 2 F)∶n(DBU) being 1.0∶1.0∶1.0∶4.0. A novel reagent for one-step O-acylation of 1,3-dicarbonyl compounds with carboxylic acids was developed. The application of R f SO 2 F in organic synthesis was further expanded.

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“…前文中我们已经报道了全氟烷基磺酰氟可以应用于活化苄醇化合物并和 1,3-二羰基化合物之间发生一步 C-或 O-苄基化反应 [12] . 作为课题研究的深入, 我们继续报道在碱性介质中, 全氟烷基磺酰 [12] , 考察了 1,3-二羰基化合物底物的适用范围.…”

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One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

严兆华¹,

王彦梅²,

金红爱³

et al. 2019

Chin. J. Org. Chem.

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View full text Add to dashboard Cite

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One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride

Abstract: C-or O-benzylation of 1,3-dicarbonyl compounds is one of the most fundamental methodologies for carbon-carbon or carbon-oxygen bond formation in organic synthesis. Perfluoroalkanosulfonyl fluoride (R f SO 2

Cited by 1 publication

References 6 publications

One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

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