☆ 4.5 Review

Bismuth(III) compounds as catalysts in organic synthesis: A mini review

POLYHEDRON (2022)

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Bismuth Redox Catalysis: An Emerging Main-Group Platform for Organic Synthesis

Hye Won Moon et al.

Summary: This article provides an overview of synthetic methodologies that capitalize on the redox cycling of bismuth. It covers different catalytic methods, mechanisms, and design strategies for stabilizing low-valent and high-valent bismuth species. Additionally, a recent example of non-redox catalysis involving bismuth is discussed. The article concludes with a discussion on opportunities and future directions in this emerging field of catalysis.

ACS CATALYSIS (2022)

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Article Chemistry, Organic

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Simone Potenti et al.

Summary: In this communication, a photoredox Barbier allylation of aldehydes mediated by bismuth is described, without the need for other metals as co-reductants. The mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Inorganic & Nuclear

Sustainable hydration of alkynes promoted by first row transition metal complexes. Background, highlights and perspectives

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Summary: The review discusses the current state of hydration reactions of alkynes catalyzed by first row transition metal complexes, focusing on examples from the last decade. It highlights the expansion of substrate scope and reaction conditions enabled by fourth period catalytic metal ions. The implications of using 3d metal complexes as alternatives to traditional noble metal catalysts for water addition reactions of alkynes are also emphasized.

INORGANICA CHIMICA ACTA (2021)

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Asymmetric Total Synthesis and Biosynthetic Implications of Perovskones, Hydrangenone, and Hydrangenone B

Baochao Yang et al.

Summary: Perovskones and hydrangenones are a family of structurally complex triterpenoids mainly isolated from Salvia medicinal plants, showing a wide range of biological activities such as antitumor and antiplasmodial activities. The total synthesis of these compounds involved asymmetric photoenolization/Diels-Alder reactions, bioinspired Diels-Alder reactions, and late-stage oxidations and ring forming steps. Studies suggest that perovskatone D may be a precursor for the biosynthesis of perovskones, while the formation of hydrangenone and hydrangenone B may involve an oxidative ring cleavage and ring regeneration process.

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Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions

Zsanett Szecsenyi et al.

Summary: Bismuth subnitrate catalyzes the atom-economical synthesis of methyl ketones via alkyne hydration, with both batch and continuous flow processes showing significant practical and sustainable advances. The catalyst's ready availability and nontoxicity eliminate the need for special additives or harmful reagents in the process.

MOLECULES (2021)

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A Mild Glycosylation Protocol with Glycosyl 1-Methylimidazole-2-carboxylates as Donors

Jianpeng Chen et al.

Summary: A mild glycosylation method using glycosyl 1-methylimidazole-2-carboxylates has been developed, with the reaction being promoted by metal triflates and triflimides, especially Cu(OTf)(2). The reaction is initiated by coordination of the glycosyl ester donor with the metal cation assisted by the adjacent 1-methylimidazole chelating group.

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Medicinal chemistry and biomedical applications of bismuth-based compounds and nanoparticles

Darren M. Griffith et al.

Summary: Bismuth, a relatively non-toxic and inexpensive metal with exceptional properties, has diverse biomedical applications ranging from treating gastrointestinal disorders to potential treatments for viral infections, multidrug resistant microbial infections, and cancer. Researchers are also exploring its applications in imaging, drug delivery, biosensing, and targeted alpha therapy.

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Bismuth(iii)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones

Digambar A. Kambale et al.

Summary: This method utilizes an unprecedented intramolecular cascade strategy to construct alpha, beta-unsaturated oxaspirolactones, using pi-electrophilic Lewis acid-catalyzed cyclization, spirolactonization steps, and semi-protected substrates can also produce oxaspirolactones under optimal reaction conditions.

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Bi(OTf)3-catalysed intramolecular cyclisation of unsaturated acetals

Raphael Saget et al.

Summary: A series of highly functionalized carbocycles were efficiently prepared via the selective cyclisation of unsaturated acetals and ketals in the presence of only 1 mol% of Bi(iii) or Fe(iii) triflates as catalysts at room temperature. Different types of products with varying yields were obtained using Bi(OTf)3 and Fe(OTf)3 catalysis.

RSC ADVANCES (2021)

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Article Chemistry, Organic

Bsi(OTf)3-mediated tandem annulation of 1-aryl isochroman-3-ones with oxygenated arenes: one-pot synthesis of polyoxygenated homotriptycenes

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Summary: The one-pot tandem annulation mediated by Bi(OTf)3 provides a highly effective method for synthesizing polyoxygenated homotriptycenes under easy-operational conditions. The protocol involves intermolecular and intramolecular Friedel-Crafts type procedures, leading to moderate to good yields in a short reaction time.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage

Angela Pacherille et al.

Summary: A simple method using BiCl3 for the cleavage of MOM ether and ester derivatives is described, resulting in good yields. Theoretical results from DFT method suggest differential initial binding site preferences of phenolic and alcoholic MOM substrates to Bi atom, and indicate the key role of water in facilitating the cleavage of the MOM group.

NEW JOURNAL OF CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Molecular bismuth(iii) monocations: structure, bonding, reactivity, and catalysis

Crispin Lichtenberg

Summary: This article summarizes the fundamental properties of well-defined molecular cationic bismuth compounds and highlights recent advancements in understanding their Lewis acidity, as well as their utilization in challenging stoichiometric reactions and catalytic applications.

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Article Chemistry, Multidisciplinary

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Summary: The paper presents a one-pot facile route for the synthesis of functionalized flavones mediated by BiCl3/RuCl3, involving intermolecular ortho-acylation of substituted phenols with cinnamoyl chlorides, and intramolecular cyclodehydrogenation of the resulting o-hydroxychalcones. The reaction conditions are discussed.

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Article Chemistry, Organic

Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides†

Hayley B. Steber et al.

Summary: The discovery of Bi(OTf)(3) as an effective catalyst for glycosyl halides activation allows for fast reactions with low catalyst amount and environmental friendliness.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Bi(OTf)3-catalysed regioselective arylation of Morita-Baylis-Hillman type allylic electrophiles

Assia Omrani et al.

TETRAHEDRON LETTERS (2020)

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Article Chemistry, Medicinal

Novel benzo[b]xanthene derivatives: Bismuth(III) triflate-catalyzed one-pot synthesis, characterization, and acetylcholinesterase, glutathione S-transferase, and butyrylcholinesterase inhibitory properties

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Liang Yang et al.

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Bismuth(III)-Catalyzed Sequential Enamine-Imine Tautomerism/2-Aza-Cope Rearrangement of Stable β-Enaminophosphonates: One-Pot Synthesis of β-Aminophosphonates

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Synthesis of Bi(III) Immobilized on Carboxyl-Terminated Triazine Dendrimer Stabilized Magnetic Nanoparticles: Improvement of Catalytic Activity for Synthesis of Indol-3-yl Acrylates

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Synthesis of 1,6-Dihydropyridine-3-carbonitrile Derivatives via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (E)-3-Amino-3-phenylacrylonitriles

Li-Juan Du et al.

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Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Oriol Planas et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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ORGANIC LETTERS (2020)

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Sustainable catalytic rearrangement of terpene-derived epoxides: towards bio-based biscarbonyl monomers

P. S. Loeser et al.

PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES (2020)

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Article Chemistry, Multidisciplinary

Bismuth(III)-Catalyzed Hydration of Terminal Alkynes: Sustainable Synthesis of Methyl Ketones in Batch and Flow

Sandor B. Otvos et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2019)

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Article Chemistry, Multidisciplinary

Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3 -Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-L-tartaric Anhydride

Babak Kaboudin et al.

ACS OMEGA (2019)

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Article Chemistry, Multidisciplinary

Bismuth(III)-Triflate-Catalyzed Highly Diastereoselective Synthesis of Substituted Tetrahydrothiophene via Tandem Isomerization, Michael and Aldol Reactions

Upasana Borthakur et al.

CHEMISTRYSELECT (2019)

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Ram Naresh Yadav et al.

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Environmentally Benign Ritter Reaction Using Bismuth Salts as a Catalyst

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Stereocontrolled Cascade Cyclisation of Campholenic Enol Ether Derivatives: En Route to Vetiver-Scented Spiroxides

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An Acid-Catalyzed Addition and Dehydration Sequence for the Synthesis of Heteroarylated Steroidal Dienes

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Bismuth(III)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans

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Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and alpha-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation

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Synthesis of heteroarylated ketones via bismuth(III) triflate-promoted regioselective 1,4-and 1,6-additions of electron-rich heteroarenes to cyclic enones and dienones

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