Bobbitt's Salt-Mediated Oxidation of Alkynyl-ols and -diols to the Corresponding Aldehydes and Their Application in Tandem Reactions

被引：2

作者：

Bobbitt, James M. ^{[1
]}

Eddy, Nicholas A. ^{[1
,2
]}

Bruckner, Christian ^{[1
]}

Bailey, William F. ^{[1
]}

Merbouh, Nabyl ^{[3
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] Univ Connecticut, Inst Mat Sci, 97 North Eagleville Rd, Storrs, CT 06269 USA

[3] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期

关键词：

ALPHA-ACETYLENIC ALDEHYDES; OXOAMMONIUM SALTS; CONVENIENT METHOD; ACETYLENEDICARBALDEHYDE; TETRAFLUOROBORATE; ALCOHOLS; REACTIVITY; REAGENT; ACCESS;

D O I：

10.1021/acs.joc.2c02828

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Propargyl alcohol derivatives were readily oxidized using Bobbitt's salt to yield the corresponding propynal products. 2-Butyn-1,4-diol may be selectively oxidized to provide either 4-hydroxy-2-butynal or acetylene dicarboxaldehyde, and the resulting stable dichloromethane solutions containing the chemically sensitive acetylene aldehydes were used directly in subsequent Wittig, Grignard, or Diels-Alder reactions. This method provides safe and efficient access to propynals and allows the preparation of polyfunctional acetylene compounds from readily accessible starting material without the use of protecting groups.

引用

页码：3321 / 3325

页数：5

共 46 条

[1] Design, synthesis, biological evaluation and molecular docking studies of novel 1H-1,2,3-Triazole derivatives as potent inhibitors of carbonic anhydrase, acetylcholinesterase and aldose reductase [J].