Triflic Acid/Silane Promoted Deoxygenative Transformation of Ketones via Carbocations

Review Chemistry, Multidisciplinary

Deoxygenative Functionalizations of Aldehydes, Ketones and Carboxylic Acids

Jianbin Li et al.

Summary: This Review covers the recent methodology development in carbonyl and carboxyl deoxygenative functionalizations, categorizing and discussing different reactive intermediates and their mechanisms.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

Molecular Iodine-Catalysed Reductive Alkylation of Indoles: Late-Stage Diversification for Bioactive Molecules

Xionglve Cheng et al.

Summary: In this study, a molecular iodine-catalysed reductive alkylation reaction of indoles with carbonyl compounds was reported for the efficient synthesis of C3-alkylated indoles. This metal-free and environmentally friendly process showed excellent functional group tolerance, mild reaction conditions, and a wide range of substrates. Importantly, the synthetic usefulness of this strategy in pharmacology was demonstrated through the late-stage modification of drug-like molecules.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Electrochemically enhanced deoxygenative cross-coupling of aryl ketones with heteroarenes through in situ generated benzyl carbocations

Yiyi Zhang et al.

Summary: Triflic acids/silanes act as cooperative reductants, allowing the convenient conversion of C=O bonds through a multistep reaction pathway in one pot. Electrolysis of the acidic reaction mixture greatly enhances carbonyl reduction, facilitating the generation of benzyl carbocations that exhibit high reactivity towards electron-rich heteroarenes for C-C bond formation.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Stereoselective Alkenylation of Ketones Mediated by Hydrazine

Shumei Xia et al.

Summary: In this study, we report an earth abundant nickel-catalyzed alkenylation of naturally abundant methylene ketones to efficiently synthesize a wide range of alkene derivatives. The protocol offers a broad substrate scope, good functional group compatibility, mild reaction conditions, water tolerance, and produces only environmentally friendly theoretical byproducts N-2, H-2, and H2O. Additionally, gram-scale synthesis with high yield and generation of pharmaceutical intermediates highlight its practical applicability.

JACS AU (2022)

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Article Multidisciplinary Sciences

C(sp3)-C(sp3) bond formation via nickel-catalyzed deoxygenative homo-coupling of aldehydes/ketones mediated by hydrazine

Dawei Cao et al.

Summary: The study presents a method for constructing C(sp(3))-C(sp(3)) bonds using a nickel-catalyzed reductive coupling of moisture and air-stable hydrazones, with broad substrate scope and harmless by-products. The method demonstrates high functional group compatibility and practicality in the application to biological molecules.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary