OXIDATION OF Α-Hydroxyketones WITH TRIPHENYLANTIMONY DIBROMIDE AND ITS CATALYTIC CYCLE

Akiba, Kin‐ya; Ohnari, Hideyuki; Ohkata, Katsuo

doi:10.1246/cl.1985.1577

Cited by 24 publications

(10 citation statements)

References 16 publications

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“…In 1982, Akiba translated a stoichiometric triphenylantimony dibromide-mediated oxidation of α-hydroxyketones to α-diketones into a catalytic protocol, employing as little as 10 mol% of the Sb(V) catalyst. 303 Upon single turnover, the resultant reducing Ph 3 Sb (Sb2) can be oxidized by the exogenous bromine surrogate 2,3-dibromo-3-phenylpropionate to regenerate the oxidizing Sb(V) dibromide (Sb1), turning over the cycle. Twenty years later, Kurita described a more practical implementation, in which 10 mol% triphenylstibine (Sb2) is used directly as catalyst under aerobic oxidation conditions to effect the same transformation in nearly quantitative yield.…”

Section: Organoantimony Redox Catalysismentioning

confidence: 99%

Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15

2021

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A growing number of organopnictogen redox catalytic methods have emergedespecially within the past 10 yearsthat leverage the plentiful reversible two-electron redox chemistry within Group 15. The goal of this Perspective is to provide readers the context to understand the dramatic developments in organopnictogen catalysis over the past decade with an eye toward future development. An exposition of the fundamental differences in the atomic structure and bonding of the pnictogens, and thus the molecular electronic structure of organopnictogen compounds, is presented to establish the backdrop against which organopnictogen redox reactivityand ultimately catalysisis framed. A deep appreciation of these underlying periodic principles informs an understanding of the differing modes of organopnictogen redox catalysis and evokes the key challenges to the field moving forward. We close by addressing forward-looking directions likely to animate this area in the years to come. What new catalytic manifolds can be developed through creative catalyst and reaction design that take advantage of the intrinsic redox reactivity of the pnictogens to drive new discoveries in catalysis?

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Section: Organoantimony Redox Catalysismentioning

confidence: 99%

Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15

2021

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“…The ultra‐centennial o ‐Iodoxybenzoic Acid (IBX) was reported as a valuable oxidant for the better conversion of benzoin into benzil [30] . Certain other reagents such as Fe(NO 3 ) 3 impregnated on acidic montmorillonite, [31] K 2 FeO 4 , [32] titanium isopropoxide, [33] benzyl triethylammonium tribromide, [34] triphenylantimony dibromide (Ph 3 SbBr 2 ), [35] Ph 3 PBr 2 [36] and PhMe 3 N + Br 3 − . NBS [37] are used to oxidize benzoin to benzil 1 in a quantitative yield.…”

Section: Methods Of Synthesis Of Benzilsmentioning

confidence: 99%

Benzils: A Review on their Synthesis

2022

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This review segregates and outlines all the aspects of the synthesis of Benzil for almost two centuries. Here, state of the art review includes the early synthesis in 1836 to the advancement made over the past years in the knowledge of the preparation of benzil derivatives till the present. Benzil is one of the important and highly underrated organic compounds in which two adjacent carbonyl groups are flanked by two phenyl rings. Apart from its diverse functionality, the reactivity of benzils proclaims its prospects as a reagent for the synthesis of various heterocycles. On recasting benzil, it is possible to obtain a wide variety of utilities in pharmaceuticals, polymer, and material chemistry. This contemplation of the review gives a general perspective of reaction routes, mechanisms and highlights the conversions due to oxidation, and accentuates benzil as an emerging putative target.

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“…99 It was reported, 100 without specifying the conditions and yields of the reaction products, that catalytic amounts of tris(2,4dibromophenyl)aminium hexachloroantimonate oxidise benzoins to the corresponding diarylethanediones. Benzoin can be oxidised with titanium isopropoxide, 101 benzyltriethylammonium tribromide, 102 triphenylstibine dibromide (Ph 3 SbBr 2 ), 103 Ph 3 PBr 2 , 104 and PhMe 3 N + Br 7…”

Section: Oxidation Of a A-hydroxycarbonyl Compoundsmentioning

confidence: 99%

Oxidative methods in the synthesis of vicinal di- and polycarbonyl compounds

Филимонов¹,

Yusubov²,

Chi³

1998

Russ. Chem. Rev.

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OXIDATION OF Α-Hydroxyketones WITH TRIPHENYLANTIMONY DIBROMIDE AND ITS CATALYTIC CYCLE

Abstract: α-Hydroxyketones were oxidized into α-diketones with triphenylantimony dibromide in the presence of two equiv. of base. Antimony-catalyzed debromination and oxidation cycle was devised for the system of ethyl 2,3-dibromo-3-phenylpropionate and α-hydroxyketones.

Cited by 24 publications

References 16 publications

Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15

Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15

Benzils: A Review on their Synthesis

Oxidative methods in the synthesis of vicinal di- and polycarbonyl compounds

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