Synthesis of Substituted Furans through Domino Aldol/Homo‐Michael Reactions of Formylcyclopropane 1,1‐Diesters with 1,3‐Dicarbonyls

Bao, Jilai; Ren, Jing; Wang, Zhongwen

doi:10.1002/ejoc.201200162

Cited by 8 publications

(1 citation statement)

References 116 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In these reactions, the heterocyclization–alkoxycarbonylation process is accompanied by dehydration, either from the R 1 CHC(2)OH moiety of 1 (resulting in aromatization and leading to 2 ) or from the MeC(2)OH moiety of 3 (leading to 4 ). To our knowledge, this is the first example of synthesis of these important classes of heterocycles via a direct carbonylation approach of acyclic precursors. − …”

Section: Introductionmentioning

confidence: 98%

Synthesis of Furan-3-carboxylic and 4-Methylene-4,5-dihydrofuran-3-carboxylic Esters by Direct Palladium Iodide Catalyzed Oxidative Carbonylation of 3-Yne-1,2-diol Derivatives

et al. 2012

View full text Add to dashboard Cite

A variety of 3-yne-1,2-diol derivatives 1, bearing a primary or secondary alcoholic group at C-1, have been efficiently converted into high value added furan-3-carboxylic esters 2 in one step by PdI(2)/KI-catalyzed direct oxidative carbonylation, carried out in alcoholic media under relatively mild conditions (100 °C under 40 atm of a 4/1 mixture of CO and air). Carbonylated furans 2 were obtained in fair to excellent isolated yields (56-93%) through a sequential 5-endo-dig heterocyclization-alkoxycarbonylation-dehydration process, using only oxygen as the external oxidant. Under similar conditions, 2-methyl-3-yne-1,2-diols 3, bearing a tertiary alcoholic group, afforded 4-methylene-4,5-dihydrofuran-3-carboxylates 4 in satisfactory yields (58-70%).

show abstract

Section: Introductionmentioning

confidence: 98%

Synthesis of Furan-3-carboxylic and 4-Methylene-4,5-dihydrofuran-3-carboxylic Esters by Direct Palladium Iodide Catalyzed Oxidative Carbonylation of 3-Yne-1,2-diol Derivatives

et al. 2012

View full text Add to dashboard Cite

show abstract

Auto‐Tandem Catalysis‐Induced Synthesis of Trisubstituted Furans through Domino Acid‐Acid‐Catalyzed Reaction of Aliphatic Aldehydes and 1,3‐Dicarbonyl Compounds by using N‐Bromosuccinimide as Oxidant

Huang

Liu

2017

Adv Synth Catal

View full text Add to dashboard Cite

The front cover picture, provided by Yanlong Gu and co-workers, illustrates the development of a method to synthesize 2,3,5-trisubstituted furans from two readily available precursors, aliphatic aldehydes and 1,3-dicarbonyl compounds. This method was established on the basis of using N-bromosuccinimide as an oxidizing reagent and aluminum(III) chloride as a catalyst. An acid-acid-catalyzed tandem reaction with auto-tandem catalysis was involved in the reaction mechanism. Details can be found in the communication on pages XXXX-

show abstract

Trifluoroacetic Acid Catalyzed Cascade Reactions of 2,3‐Diketoesters with Cyclohexane‐1,3‐diones: Strategy Towards 4‐Hydroxybenzofuran Derivatives

Sha

Liu

2019

Adv Synth Catal

View full text Add to dashboard Cite

An efficient trifluoroacetic acid catalyzed cascade reaction of 2,3-diketoesters with cyclohexane-1,3-diones is described for the synthesis of a series of 4-hydroxybenzofurans. This simple protocol has the advantages of easy operation, readily available starting materials, good functional group tolerance, and easily scale-up. Subsequent derivatization of the 4-hydroxybenzofurans provides a reasonable route to access highly functionalized benzofurans.

show abstract

Synthesis of Substituted Furans through Domino Aldol/Homo‐Michael Reactions of Formylcyclopropane 1,1‐Diesters with 1,3‐Dicarbonyls

Abstract: A Lewis acid catalyzed domino aldol/homo‐Michael reaction of formylcyclopropane 1,1‐diesters with dicarbonyls has been successfully developed. This method provides efficient and direct construction of highly functionalized furans from easily available starting materials.

Cited by 8 publications

References 116 publications

Synthesis of Furan-3-carboxylic and 4-Methylene-4,5-dihydrofuran-3-carboxylic Esters by Direct Palladium Iodide Catalyzed Oxidative Carbonylation of 3-Yne-1,2-diol Derivatives

Synthesis of Furan-3-carboxylic and 4-Methylene-4,5-dihydrofuran-3-carboxylic Esters by Direct Palladium Iodide Catalyzed Oxidative Carbonylation of 3-Yne-1,2-diol Derivatives

Auto‐Tandem Catalysis‐Induced Synthesis of Trisubstituted Furans through Domino Acid‐Acid‐Catalyzed Reaction of Aliphatic Aldehydes and 1,3‐Dicarbonyl Compounds by using N‐Bromosuccinimide as Oxidant

Trifluoroacetic Acid Catalyzed Cascade Reactions of 2,3‐Diketoesters with Cyclohexane‐1,3‐diones: Strategy Towards 4‐Hydroxybenzofuran Derivatives

Contact Info

Product

Resources

About