5,5',5''-(((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(oxy))triisophthalic acid
CAS Number:
1159974-70-5
Molecular Formula:
C36H30O15
Olefination of aldehydes with alpha-halo redox-active esters
Literature Information
Publication Date
2023-12-14
DOI
10.1039/D3QO01805A
Impact Factor
5.281
Authors
Zhengqiang Liu, Wenbo H. Liu
View Original
Abstract
Olefin synthesis is a fundamentally important process in organic chemistry. Among the numerous approaches to obtaining olefins such as alcohol/halide eliminations, alkyne-based reductions and additions, pericyclic reactions, metal-mediated cross-couplings, olefin metathesis, etc., carbonyl olefinations are particularly of significance, as exemplified by the Wittig-type reactions. In this report, we describe a new decarboxylative carbonyl olefination in one step with a broad substrate scope under mild conditions by merging an aldehyde and the α-halo carboxylic N-hydroxyphthalimide (NHPI) ester. Mechanistic investigations reveal that this reaction takes place via a tandem nucleophilic addition/reductive E1cb process. The operational simplicity, the ready availability of both starting materials and the versatility of the olefin product demonstrate the potential synthetic utility of this decarboxylative carbonyl olefination.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
1-(3,4-Dichlorophenyl)-1H-pyrazole-3-carboxylic acid
CAS Number:
1152949-12-6
Molecular Formula:
C10H6Cl2N2O2
4-(Dimethylaminomethyl)phenylacetic acid hydrochloride
CAS Number:
99985-52-1
Molecular Formula:
C11H16ClNO2
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