Catalytic α-hydroxylation of ketones under CuBr2 or HBr/DMSO systems

Li, Hongliang; An, Xing‐Lan; Ge, Li‐Shi; Luo, Xiaoyan; Deng, Wei‐Ping

doi:10.1016/j.tet.2015.03.116

Cited by 41 publications

(15 citation statements)

References 61 publications

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“…In this regard, and in addition to the previously mentioned examples, the groups of Cao and Deng have developed further protocols for the α-oxidation of ketones with DMSO and HBr. 188,189 Similar results were obtained by Jiao and co-workers, achieving selective α-hydroxylation of linear and α-branched ketones ( 347 ), using substoichiometric amounts of iodine and a large excess of DMSO (Scheme 55a). 190 In situ 1,2-dicarbonyl formation was additionally exploited in Wu and co-workers’ oxazole synthesis, as shown in Scheme 55b.…”

Section: Sulfoxidessupporting

confidence: 76%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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Section: Sulfoxidessupporting

confidence: 76%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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“…In this reaction, the simple I 2 /NBS was used as the catalyst and DMSO serves as the oxygen source, oxidant and solvent (Scheme c). A similar kind of work was also reported with CuBr 2 or HBr as the catalyst in DMSO by Deng, Luo and their co‐workers 59…”

Section: As Oxidantsupporting

confidence: 63%

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

2016

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Dimethyl sulfoxide (DMSO) is one of the most commonly applied organic solvents in chemical transformationsa nd is utilized widely in industrial processesa sw ell. During the past decades,n umerous procedures using DMSO as ar eaction reagent have been developed and published.I nt his review,t he main developmentso nt he employment of DMSOa s sources of À Me, À SMe, À SO 2 Me,a sa no xidant etc. have been summarized and discussed.1I ntroduction 2A sC 1 Sources 2.1 As À CH 3 S ource 2.2 As À CH 2 À S ource 2.3 As À CH À S ource 2.4 As À CHO Source 2.5 As À CNS ource 3A s S(O) x Me Sources 3.1 As À SMe Source 3.2 As À SO 2 Me Source 4A sO xidant 4.1 As Oxygen Source 4.2 As Oxidant 5C onclusions

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“…Our previous works howed that both allylic CÀHa nd a-car-bonylC ÀHb onds could be easily activated to form free radi-cals or carbeniumi ons under oxidative reactionc onditions; [11] this was also demonstrated by other groups. [12] Based on these findings, we envisioned that the a-carbona nion of intermediate A3,d erived from nucleophilic addition of ab isnucleophile to an allene-1,3-dicarboxylice ster,c ould be inverted into ac arbenium ion under oxidative conditions and subsequentlya ttacked by another nucleophilic site to afford the cyclization product [Scheme 1, Eq.…”

Section: Introductionmentioning

confidence: 66%

“…Chem. Eur.J.2016, 22,9 348 -9355 www.chemeurj.org thoxyl, halogeno, trifluoromethyl, and nitro, on the aryl group of the benzoylacetate esters were well tolerated under optimized conditions ( Table 3, entries [1][2][3][4][5][6][7][8][9][10][11]. Similarly,asymmetric b-diketone, 4l,w as also as uitable substrate, affording the corresponding product 5l in 67 %y ield.…”

Section: Resultsmentioning

confidence: 99%

α,β‐Double Electrophilic Addition of Allene‐1,3‐Dicarboxylic Esters for the Construction of Polysubstituted Furans by KI/tert‐Butyl Hydroperoxide (TBHP)‐Promoted Oxidative Annulation

Wang

Sun

et al. 2016

Chemistry A European J

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An unprecedented KI/tert-butyl hydroperoxide promoted tandem Michael addition/oxidative annulation of allene-1,3-dicarboxylic esters and 1,3-dicarbonyl compounds has been developed. This procedure provides a new, facile, and transition-metal-free synthetic approach to afford polysubstituted furans in moderate to excellent yields (up to 93 %). This method first establishes a α,β-double electrophilic reaction mode of allene-1,3-dicarboxylic esters to form 1,3-dicarbonyl compounds.

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Catalytic α-hydroxylation of ketones under CuBr2 or HBr/DMSO systems

Cited by 41 publications

References 61 publications

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

α,β‐Double Electrophilic Addition of Allene‐1,3‐Dicarboxylic Esters for the Construction of Polysubstituted Furans by KI/tert‐Butyl Hydroperoxide (TBHP)‐Promoted Oxidative Annulation

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