Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones

Lima, Samia R.; Coelho, Fernando

doi:10.1021/acsomega.0c00101

Cited by 3 publications

(4 citation statements)

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“…The silylation reagent can be eliminated by using an acyloxy group at the γ-position of the unsaturated ketone, it is possible in this way to convert (E)-4-acetoxy-1-phenyl-2-buten-1-one into the desired 1,3-diketone with 91% yield while working in THF at room temperature for 2 h (Scheme 13a) [94]. This methodology was extended to the preparation of other 1,3-diketones (86). Aryl enones led to the final products with excellent yields (84-99%), whereas those alkylic ones afforded the diketones with moderate yields (51-69%).…”

Section: Miscellaneous Methodologiesmentioning

confidence: 99%

“…The hydration of these compounds leads to the formation of 1,3-diketones, but the requirement of strong acidic conditions or the presence of PtCl 4 or amines as catalysts reduces the application of this synthetic methodology. For this reason, in the last years, some other approaches for the hydration of alkynones under mild reaction conditions have been described [86,87].…”

Section: Synthesis Of 13-diketones By Hydration Of Alkynonesmentioning

confidence: 99%

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Recent Developments in the Synthesis of β-Diketones

Gonzalo

Alcántara

2021

Pharmaceuticals

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Apart from being one of the most important intermediates in chemical synthesis, broadly used in the formation of C–C bonds among other processes, the β-dicarbonyl structure is present in a huge number of biologically and pharmaceutically active compounds. In fact, mainly derived from the well-known antioxidant capability associated with the corresponding enol tautomer, β-diketones are valuable compounds in the treatment of many pathological disorders, such as cardiovascular and liver diseases, hypertension, obesity, diabetes, neurological disorders, inflammation, skin diseases, fibrosis, or arthritis; therefore, the synthesis of these structures is an area of overwhelming interest for organic chemists. This paper is devoted to the advances achieved in the last ten years for the preparation of 1,3-diketones, using different chemical (Claisen, hydration of alkynones, decarboxylative coupling) or catalytic (biocatalysis, organocatalytic, metal-based catalysis) methodologies: Additionally, the preparation of branched β-dicarbonyl compounds by means of α-functionalization of non-substituted 1,3-diketones are also discussed.

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Section: Miscellaneous Methodologiesmentioning

confidence: 99%

Section: Synthesis Of 13-diketones By Hydration Of Alkynonesmentioning

confidence: 99%

Recent Developments in the Synthesis of β-Diketones

Gonzalo

Alcántara

2021

Pharmaceuticals

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“…Very recently, Lima and Coelho reported the α-hydration of alkynes 71 leading regioselectively to 1,3-ketoesters 72 in excellent yields (Scheme 41). 83 Among the gold catalysts tested to perform this regioselective hydration reaction, Et 3 PAuCl associated with AgOTf was found to be the most efficient combination. This α-hydration is explained by the assistance of the ester function (CO 2 R) leading exclusively to the formation of a five- Moreover, this catalytic process tolerates many aromatic (72a,b), heteroaromatic (72d), or alkyl substituents (72c).…”

Section: Hydration Of Alkynes Directed By An Ester Functionmentioning

confidence: 99%

Hydration of Unsymmetrical Internal Alkynes: Factors Governing the Regioselectivity

et al. 2023

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Water addition on an unsymmetrical internal alkyne has significance in organic chemistry and has stimulated challenging approaches to access a highly regioselective process. Hydration or formal hydration is presented according to the type of internal alkyne. Methods for electron-rich and -poor diarylalkynes followed by those adapted to arylalkylalkynes are presented. Regioselective hydration reactions of unsymmetrical propargylic and homopropargylic derivatives are then discussed, followed by regioselective aspects of the hydration of internal alkynes directed by carbonyl groups. The following section examines the hydration alkynes linked to CF 3 , esters, ketones, and heteroatoms as haloalkynes, alkynylphosphonates, ynamides, and others. At the end of this section, we report some recent examples of hydration reactions where the alkyne triple bond is connected to an electron-withdrawing group as an ester or a ketone. Reactions are presented, discussed, and illustrated in each of these items through various representative examples. The mechanistic hypotheses explaining the origin of the regioselectivity in the hydration reactions are discussed. This review of recent advances in the regioselective hydration of internal unsymmetrical alkynes (from 2007 until the present) aims to update the current body of knowledge and aid researchers working in this field.

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“…Tricarbonyl compounds have been used for the synthesis of functionalized biphenyls via an oxidative aromatization with iodine 8 a and for the formal synthesis of (±)-cochlearol A. 8 b The oxidation of tricarbonyl compounds has been used for the preparation of propellanes, compounds showing a broad spectra of biological and pharmacological activities, 8 c as well as for the synthesis of heterocycles.…”

Section: Introductionmentioning

confidence: 99%