Boron-Based Lewis Acid Catalysis: Challenges and Perspectives

Catalysts, Год журнала: 2021, Номер 12(1), С. 5 - 5

Опубликована: Дек. 22, 2021

In the last two decades, boron-based catalysis has been gaining increasing traction in field of organic synthesis. The use halogenated triarylboranes as main group Lewis acid catalysts is an attractive strategy. It applied a growing number transformations over years, where they may perform comparably or even better than gold standard catalysts. This review discusses methods borane synthesis and cutting-edge catalysis, focusing especially on tris(pentafluorophenyl)-borane [B(C6F5)3], other triarylboranes, highlighting how boron acids employed can unlock plethora unprecedented chemical improve efficiency existing reactions.

Язык: Английский

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Borane-catalysed S–H insertion reaction of thiophenols and thiols with α-aryl-α-diazoesters

Green Synthesis and Catalysis, Год журнала: 2021, Номер 2(4), С. 385 - 388

Опубликована: Окт. 13, 2021

Herein, we have developed a novel B(C6F5)3-catalysed S–H bond insertion of thiophenols and thiols with α-aryl-α-diazoesters under mild conditions, furnishing various sulfides in moderate to excellent yield. This method features simple operation, broad substrate scope easy scale-up, which provide an alternative approach for transition-metal catalysed reaction.

Язык: Английский

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Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors

ACS Catalysis, Год журнала: 2021, Номер 12(1), С. 442 - 452

Опубликована: Дек. 17, 2021

Reactive carbenes generated from diazo compounds are key intermediates for a range of organic reactions to afford synthetically useful compounds. The majority these have been carried out using transition metal catalysts. However, the formation carbene main group elements has not widely investigated synthetic purposes. Recent studies demonstrated that triarylboranes can be used in situ generation reactive both stoichiometric and catalytic reactions. These new reactivities gained significant attention chemistry particularly studies. synthesized through important as pharmaceuticals or agrochemicals. In this perspective, we highlight recent progress ongoing challenges transfer their corresponding precursors We also use which boranes only activate functionality intermediate but actively participate reagent. different mechanisms activation described along with mechanistic computational aided elucidation reaction pathways. Potential opportunities catalyst toward future prospects discussed.

Язык: Английский

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General Ir-Catalyzed N–H Insertions of Diazomalonates into Aliphatic and Aromatic Amines

Organic Letters, Год журнала: 2024, Номер 26(5), С. 983 - 987

Опубликована: Янв. 26, 2024

A general N–H insertion reactivity of acceptor–acceptor diazo malonate reagents is reported using [Ir(cod)Cl]2 as catalyst. large range amines, primary and secondary, aliphatic aromatic, possible. Mild temperatures, perfect substrate/reactant stoichiometry, good functional group compatibility render the process particularly attractive for (late-stage) functionalization amines.

Язык: Английский

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B(C6F5)3-catalyzed selective C–H chalcogenation of arenes and heteroarenes

Chem, Год журнала: 2024, Номер 10(9), С. 2901 - 2915

Опубликована: Июнь 27, 2024

The synthesis of organochalcogenides remains a valuable area research due to their widespread biological applications, particularly in pharmaceuticals. Herein, our study details the B(C6F5)3-catalyzed Csp2–H functionalization diverse arenes, heteroarenes, and pharmacophores with thiosuccinimides or selenosuccinimides, providing selective access chalcogenated products. This protocol enables late-stage chalcogenation drug molecules such as anti-inflammatory naproxen, estrogen steroid hormone estradiol derivatives, industrially relevant trifluoromethylthiolation reaction. Furthermore, this C–S coupling methodology provides facile metal-free route synthesize vortioxetine, an antidepressant drug, plethora significant organic motifs. Detailed NMR, EPR analyses, density functional theory (DFT) computational studies indicate that elongation thiosuccinimide N–S bond is assisted by boron-centered adduct, which then leads stable ion pair arene. analysis shows transient radical pair, potentially off-cycle species, not directly involved catalytic process.

Язык: Английский

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Chiral phosphoric acid-catalyzed atroposelective oxidative coupling of carbazoles

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 14, 2025

Язык: Английский

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Copper(II) NHC pincer complexes containing 1,2,3-triazole units: Synthesis, structure and catalysis for C N bond forming reactions

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155588 - 155588

Опубликована: Апрель 1, 2025

Язык: Английский

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B(C₆F₅)₃-catalyzed Wolff rearrangement/[2 + 2] and [4 + 2] cascade cyclization of α-diazoketones with imines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1754 - 1758

Опубликована: Янв. 1, 2023

B(C 6 F 5 ) 3 -catalyzed [2 + 2] cyclizations of α-diazoketones with N-tert -butoxycarbonyl imines affords 20 β-lactams in up to 94% yield, while reactions N -benzoyl gave 14 oxazinone derivatives 95% yield.

Язык: Английский

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Tris(pentafluorophenyl)borane‐Catalyzed Carbenium Ion Generation and Autocatalytic Pyrazole Synthesis—A Computational and Experimental Study

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(46), С. 24395 - 24399

Опубликована: Сен. 30, 2021

In recent years, metal-free organic synthesis using triarylboranes as catalysts has become a prevalent research area. Herein we report comprehensive computational and experimental study for the highly selective of N-substituted pyrazoles through generation carbenium species from reaction between aryl esters vinyl diazoacetates in presence catalytic tris(pentafluorophenyl)borane [B(C6 F5 )3 ]. DFT studies were undertaken to illuminate mechanism revealing that situ acts an autocatalyst prompt regiospecific formation good excellent yields (up 81 %).

Язык: Английский

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Access to Azepino-Annulated Benzo[c]carbazoles Enabled by Gold-Catalyzed Hydroarylation of Alkynylindoles and Subsequent Oxidative Cyclization

Organic Letters, Год журнала: 2022, Номер 24(36), С. 6505 - 6509

Опубликована: Сен. 1, 2022

Herein, we report a facile and efficient synthetic method to construct azepino[1,2-a]indoles through novel gold(I)-catalyzed intramolecular hydroarylation of alkynylindoles. A wide range functional groups can be well tolerated in this transformation, the corresponding highly functionalized azepino[1,2-a]indole skeletons were obtained moderate excellent yields. Subsequent oxidation products gave interesting valuable polycyclic carbazoles, which widely used as key building blocks materials science.

Язык: Английский

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