Convenient thiocyanation of indoles in CeBr3/H2O2 system

Article Biochemistry & Molecular Biology

Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions

Qing Huang et al.

Summary: An efficient and general method has been developed for the synthesis of various organic compounds, featuring simple operation, metal-free and iodine-free conditions.

MOLECULES (2022)

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Article Chemistry, Organic

Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?

Chenxi He et al.

Summary: In this study, the authors reinvestigated the green alcohol oxidation method using FeBr3(cat.)/H2O2 and proposed a different mechanism involving a reactive brominating species (RBS). They provided evidence to support this RBS-based mechanism and discovered that a RBS generated from CeBr3/H2O2 is more efficient for the oxidation of secondary and benzylic alcohols, presenting a new green protocol for selective alcohol oxidation to carbonyls.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones

Zhihua Qiao et al.

Summary: A Lewis acid-catalyzed cyclization reaction has been achieved under mild conditions, leading to the synthesis of functionalized spirocyclohexadienone precursors. This method offers moderate to excellent yields and exhibits good functional group tolerance towards a wide range of substrates.

TETRAHEDRON LETTERS (2022)

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Article Chemistry, Organic

Sulfated polyborate catalyzed rapid and efficient electrophilic thiocyanation of activated arenes

Nilesh B. Patil et al.

Summary: This study presents a rapid, efficient, and environmentally friendly method for electrophilic thiocyanation of activated arenes. The method utilizes sulfated polyborate as a Bronsted acid catalyst and H2O2 as a green oxidizer. It shows promising results for various activated arenes and allows for recyclability of the aqueous solution, offering easy operation under mild reaction conditions.

TETRAHEDRON LETTERS (2022)

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Review Chemistry, Multidisciplinary

Design and Use of Electrophilic Thiocyanating and Selenocyanating Reagents: An Interesting Trend for the Construction of SCN- and SeCN-Containing Compounds

Melissa Gao et al.

Summary: Organothiocyanate and organoselenocyanate compounds are important in organic chemistry as key intermediates for accessing sulfur- and selenium-containing compounds. Recent research has focused on original methodologies using electrophilic reagents to synthesize SCN- and SeCN-containing molecules. This review highlights the design of electrophilic sources and their applications in thiocyanation and selenocyanation of various compound classes.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Review Chemistry, Organic

A Review on Thiocyanation of Indoles

Chitteti Divyavani et al.

Summary: This review highlights various methods for the thiocyanation of indoles and emphasizes the importance of studying new approaches for the preparation of 3-thiocyanato-indoles. The mechanistic aspects and significance of these methods are also briefly discussed.

CURRENT ORGANIC SYNTHESIS (2021)

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Article Chemistry, Physical

Fenton Chemistry for Achmatowicz Rearrangement

Guodong Zhao et al.

Summary: The Achmatowicz rearrangement is a significant transformation for the synthesis of various heterocyclic building blocks and natural products. The discovery of Fenton chemistry for AchR using a bifunctional catalyst has environmental friendliness and a broad substrate scope, addressing limitations of conventional chemical and enzymatic methods. Reactice brominating species (RBS) is found to be the true catalyst for AchR, and the in situ RBS generation from M-Br-x-H2O2 under neutral conditions solves the longstanding issue of acidic additives required for bromide oxidation with H2O2, creating opportunities for other bromine-mediated organic reactions.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

From Reactive Oxygen Species to Reactive Brominating Species: Fenton Chemistry for Oxidative Bromination

Guodong Zhao et al.

Summary: Fenton chemistry can generate reactive brominating species under neutral conditions, addressing the safety and environmental challenges of existing oxidative bromination methods. This new method for generating RBS will significantly benefit the wide applications of brominated organic compounds in various industries.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

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Article Chemistry, Multidisciplinary

Isoquinolinium-N-sulfonic acid thiocyanate/H2O2 as efficient reagent for thiocyanation of N-bearing (hetero)aromatic compounds

Sobhan Rezayati et al.

Summary: In this study, isoquinoline sulfonic acid thiocyanate and isoquinoline sulfonic acid chloride were successfully synthesized as novel heterogeneous catalysts for the synthesis of thiocyanate derivatives. These catalysts offer a simple and convenient reaction process, utilizing commercially available materials, cheap and chemically stable reagents, short reaction time, and excellent yield.

JOURNAL OF SULFUR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide

Guodong Zhao et al.

Summary: This study reports a green catalytic oxidative rearrangement of indoles, which has wide substrate scope and environmental friendliness. The reactive brominating species generated by Fenton chemistry serves as the catalyst for the oxidative rearrangement under neutral conditions.

GREEN CHEMISTRY (2021)

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Article Chemistry, Organic