Iodine-catalysed regioselective synthesis of β -hydroxysulfides

Tehri, Piyush; Aegurula, Balakrishna; Peddinti, Rama Krishna

doi:10.1016/j.tetlet.2017.04.043

Cited by 25 publications

(14 citation statements)

References 47 publications

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“…0]octane (2). Oxone (169 mmol) was slowly added by portions to a stirred solution of 1,3-dioxacyclohept-5-en 1 (130.2 mmol) and NaHCO 3 (619 mmol) in 100 ml of acetone-water mixture (1 : 1 v/v) for 3 hours at 20°C.…”

Section: Methodsmentioning

confidence: 99%

“…Yield 93%, colorless oil. 1 4.74 and 4.77 (AB, 2O, 2O 2 , 2 J(O 2 A O 2 C ) � −4.5 Hz), 7.24-7.48 m (5O, S 6 O 5 ). 13 C NMR (CDCl 3 ), δ: 54.63 (S 6 ), 65.32 (S 7 ), 66.39 (S 4 ), 71.34 (S 5 ), 94.07 (S 2 ), 127.32 (C Ar ), 129.05 (C Ar ), 131.73 (C Ar ), 133.22 (C Ar ).…”

Section: -(Phenylthio)-13-dioxepan-5-ol (3) (1) General Procedures mentioning

confidence: 99%

“…β-Hydroxysulfides are attractive tools in organic synthesis, which are actively used in the synthesis of allylic alcohols, cyclic sulfides, thioketones, and physiologically active compounds [1][2][3][4][5]. Products of their oxidation, β-hydroxysulfones, are useful reagents for preparation of lactones [6], 2,5disubstituted tetrahydrofuranes [7], and vinyl sulfones [8].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Antifungal Activity of β-Hydroxysulfides of 1,3-Dioxepane Series

Pavelyev

Vafina

Balakin

et al. 2018

Journal of Chemistry

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Section: Methodsmentioning

confidence: 99%

Section: -(Phenylthio)-13-dioxepan-5-ol (3) (1) General Procedures mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Antifungal Activity of β-Hydroxysulfides of 1,3-Dioxepane Series

Pavelyev

Vafina

Balakin

et al. 2018

Journal of Chemistry

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“…An easy method to prepare b-hydroxy sulfidesf rom thiols and styrenes has been reported (Scheme 72). [96] Thiols and styrenes with electron-rich substituents and halidesh ave been examined, and they provide the corresponding products in good to excellenty ields. Electrophilic iodo species 413 generated from thiol 412 liberates thio radical 414,w hich reacts with styrene 415 to form benzylic radical 416.D MSOt hen attacks 416 to produce intermediate 417,w hich in the presenceo fi nsitu generated HI is convertedi nto product 418 andr egenerates I 2 .…”

Section: Heteroatom Activation To Form Ah Etàibond As Ak Ey Intermediatementioning

confidence: 99%

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

Parvatkar

Manetsch

Banik

2018

Chemistry An Asian Journal

102

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The development of ecofriendly methods for carbon-carbon (CÀC) and carbon-heteroatom (CÀHet) bond formation is of great significance in modern-dayr esearch. Metal-free cross-dehydrogenative coupling (CDC) has emerged as an important tool for organic and medicinal chemists as am eanst of orm CÀCa nd CÀHet bonds, as it is atom economical and more efficient and greenert han transition-metalc atalyzed CDC reactions. Molecular iodine (I 2 )i s recognized as an inexpensive, environmentally benign, and easy-to-handle catalyst or reagentt op ursueC DCs under mild reactionc onditions, with good regioselectivities and broad substrate compatibility.T his review presentst he recentd evelopmentso fI 2 -catalyzed CÀC, CÀN, CÀO, and CÀ S/CÀSe bond-forming reactions for the synthesis of various important organic molecules by cross-dehydrogenative coupling.Scheme1.Strategies for CÀCa nd CÀHet bond formation by CDC.[a] Dr. Scheme5.Synthesis of substituted indolizines.Scheme6.Synthesis of (E)-or (Z)-2-methylthio-1,4diones.Scheme7.Synthesis of indolo[2,3-b]carbazoles.Scheme8.Synthesis of p-amino phenyl diketones.Scheme9.Synthesis of functionalized cyclopropanes.Scheme10. Photooxidative coupling of thiophenesw ith carbonyls.Bz = benzoyl.Scheme65. Synthesis of 2-aminobenzothiazoles. PTSA = para-toluenesulfonic acid.Scheme66. Synthesis of b-decarbonylated sulfones.Scheme67. Synthesis of diheteroaryl thioethers.

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“…In 2019, Ai‐Bao Xia and co‐workers have synthesized dihydrofuropyrimidines and spirodihydrofuropyrimidine pyrazolones with good yields using molecular iodine as a catalyst which is metal free, easy to carry out, substrate easiness, diastereoselective and chemoselective . The recent literature discloses that molecular iodine can be employed as an efficient catalyst for diverse multicomponent reactions– and synthesis of different heterocycles –. The mild Lewis acidity associated with iodine has led to its use in the organic synthesis using catalytic to stoichiometric amounts .…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Three‐Component Synthesis of 3‐Aminoalkyl Indoles Catalyzed by Molecular Iodine

Depa

Erothu

2019

ChemistrySelect

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A facile one‐pot three‐component coupling (3CC) of indoles, aldehydes, and N‐alkyl anilines has been attained using a catalytic quantity of molecular iodine under neutral conditions to afford 3‐aminoalkyl indoles at room temperature. The salient features of this method are the mild reaction conditions, the operational simplicity of the method, outstanding yields in moderately at short reaction times and low cost of the catalyst.

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Iodine-catalysed regioselective synthesis of β -hydroxysulfides

Cited by 25 publications

References 47 publications

Synthesis and Antifungal Activity of β-Hydroxysulfides of 1,3-Dioxepane Series

Synthesis and Antifungal Activity of β-Hydroxysulfides of 1,3-Dioxepane Series

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

One‐Pot Three‐Component Synthesis of 3‐Aminoalkyl Indoles Catalyzed by Molecular Iodine

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