Synthetic Methods and Reactions; 70<sup>1</sup>. Oxidation of Thiols to Disulfides with Bromodimethylsulfonium Bromide

Oláh, George A.; Arvanaghi, Massoud; Vankar, Yashwànt D.

doi:10.1055/s-1979-28812

Cited by 44 publications

(25 citation statements)

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“…The first use of this reagent was reported by Olah et al in 1979, for the oxidation of thiols to disulfides and the conversion of epoxides and enamines into α‐halo ketones . Noticeable growth in the application of this reagent in organic synthesis has been observed in recent years (Scheme ) .…”

Section: Lewis‐base‐coordinated Halogen(i) Intermediates Generatedmentioning

confidence: 99%

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

et al. 2017

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The widespread use of halogen‐based reagents in organic synthesis is well known. Hypervalent halogens (oxidation states III and V) have been explored to a significant extent. Among them, hypervalent iodine reagents have found major use and applications. In contrast, understanding of the reactivity of halogen(I) species in the presence of Lewis bases, and their reaction mechanisms, are very limited. This microreview sheds light on the importance of halogen(I) species and their applications in organic synthesis. In commercially available halogen(I) precursors such as N‐halosuccinimides, the halogen atom is attached to the nitrogen atom through a covalent bond with low electrophilicity and thus low reactivity. Interestingly, the reactivity increases if the electrophilic halogen(I) atom is attached to a Lewis base through a polarized covalent bond. The halogen‐bonding interaction between the Lewis base and the halonium ion (or halonium ion equivalent) results in highly reactive and thermodynamically stable halogen(I) intermediates that act as versatile reagents. This microreview unravels the evolution of the unstable halogen(I) intermediates to become versatile reagents.

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Section: Lewis‐base‐coordinated Halogen(i) Intermediates Generatedmentioning

confidence: 99%

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

et al. 2017

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“…(Table 4, entry 7): [51] 100 mL of stock solution C were used; column chromatography hexane/ethyl acetate 50:1; white solid (95 % yield). 1 (Table 4, entry 8): [52] 100 mL of stock solution C and LiHMDS (184 mg, 1.10 mmol) were used; column chromatography; hexane; colorless liquid (93 % yield). (Table 4, entry 10): [28] 250 mL of stock solution C were used; column chromatography: hexane/ethyl acetate 50:1;: white solid (99 % yield).…”

Section: -Methyl-2-propyl 4-trifluoromethylphenyl Sulfide (mentioning

confidence: 99%

Highly Efficient and Functional‐Group‐Tolerant Catalysts for the Palladium‐Catalyzed Coupling of Aryl Chlorides with Thiols

Fernández‐Rodríguez

Shen

Hartwig

2006

Chemistry A European J

266

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The cross-coupling reaction of aryl chlorides with aliphatic and aromatic thiols catalyzed by palladium complexes of the strongly binding bisphosphine CyPF-tBu ligand (1) is reported. Most of the reactions catalyzed by complexes of ligand 1 occur with turnover numbers that exceed those of previous catalysts by two orders of magnitude. The reactions occur with excellent yields, broad scope and high tolerance of functional groups. Coupling of aryl halides with thiols in the presence of low loadings of catalysts derived from other Josiphos type ligands, as well as ligands of other structural types, are also described.

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“…The supernatant contained (TLC estimation) bis(2-pyridyl) disulfide (∼15%) and 2-mercaptopyridine (∼85%) and gave a solid, which melted at 118-121 • C. Pure disulfide melts at 52-53 • C 49 and pure thiol melts at 128-130 • C. 50 To the ester 8 (0.25 mmol) dissolved in dry dichloromethane (18 mL) oxygen was added, stoppered, and stirred at r.t. for 48 h. Centrifugation and washing with chloroform gave pure, by IR, As 2 O 3 (23 mg), corresponding to 94% decomposition. The supernatant contained (by TLC) the disulfide (∼70%) and thiol plus 8 (∼30%) and gave a solid, which melted at 45-47 • C.…”

Section: Tris(2-pyridyl) Trithioarsenitementioning

confidence: 99%

The Autoxidation of Triaryl Trithioarsenites, (ArS)₃As: Evidence for Binding and Activation of Triplet Dioxygen by Arsenic(III)

Haikou

Ioannou

2006

Phosphorus, Sulfur, and Silicon and the Related Elements

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Synthetic Methods and Reactions; 70¹. Oxidation of Thiols to Disulfides with Bromodimethylsulfonium Bromide

Cited by 44 publications

References 0 publications

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

Highly Efficient and Functional‐Group‐Tolerant Catalysts for the Palladium‐Catalyzed Coupling of Aryl Chlorides with Thiols

The Autoxidation of Triaryl Trithioarsenites, (ArS)₃As: Evidence for Binding and Activation of Triplet Dioxygen by Arsenic(III)

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Synthetic Methods and Reactions; 701. Oxidation of Thiols to Disulfides with Bromodimethylsulfonium Bromide

Cited by 44 publications

References 0 publications

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

Highly Efficient and Functional‐Group‐Tolerant Catalysts for the Palladium‐Catalyzed Coupling of Aryl Chlorides with Thiols

The Autoxidation of Triaryl Trithioarsenites, (ArS)3As: Evidence for Binding and Activation of Triplet Dioxygen by Arsenic(III)

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Synthetic Methods and Reactions; 70¹. Oxidation of Thiols to Disulfides with Bromodimethylsulfonium Bromide

The Autoxidation of Triaryl Trithioarsenites, (ArS)₃As: Evidence for Binding and Activation of Triplet Dioxygen by Arsenic(III)