Recent advances of carbonyl olefination <i>via</i> McMurry coupling reaction

Bongso, Anthony; Roswanda, Robby; Syah, Yana Maolana

doi:10.1039/d2ra00724j

Cited by 25 publications

(15 citation statements)

References 109 publications

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“…[128][129][130][131] This reaction is a one-electron process widely used to form symmetrical olefins. 132 The case of its utilization in the synthesis of polymers was reported by Rusli Daik et al 133 in 2004, and the reaction successfully obtained poly(4,4-diphenylene diphenylvinylene) (Figure 23(a)). Recently, Sentaro Okamoto's group began to study the application value of this reaction in polymer synthesis.…”

Section: Mcmurry Couplingmentioning

confidence: 87%

Advances in the application of named reactions in polymer synthesis

Zou

2022

High Performance Polymers

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With the development of polymer science, more and more named reactions have been applied to synthesizing polymers. Introducing new reactions into polymer synthesis is undoubtedly an excellent expansion for monomer and polymer libraries. In this review, the named reactions employed in polymer-chain synthesis were divided into seven types: electrophilic reactions, nucleophilic reactions, transition metal-mediated cross-coupling reactions, free radical reactions, pericyclic reactions, multi-component reactions and rearrangement reactions. The discussion was mainly focused on the progress in the utilization of these named reactions in polymer synthesis, which could be a valuable reference for researchers in the polymer field.

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Section: Mcmurry Couplingmentioning

confidence: 87%

Advances in the application of named reactions in polymer synthesis

Zou

2022

High Performance Polymers

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“…Subsequently, 29 was subjected to the pyrrole [3+2] ring‐forming process using tosylmethyl isocyanide and trimethyltin chloride, under basic conditions, and finally copper (II) nitrate was added, in order to obtain 30 . The last step involved Vilsmeier‐Hack formylation [76] (POCl 3 , DMF) of 31 followed by McMurry reductive cyclization, [77] using TiCl 4 , of 32 to afford porphycene 33 in 25 % yield (Scheme 15).…”

Section: Synthetic Methods For Structural Modulation Of Tetrapyrrolic...mentioning

confidence: 99%

Synthesis of Photosensitizers Based on Tetrapyrrolic Macrocycles for Combination with Antibiotics: Dual Inactivation of Bacteria

et al. 2022

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The combination of photodynamic therapy with antibiotics or antimicrobial peptides for inactivation of bacteria is an area of growing interest due to the synergistic effect already observed by many authors. It has been shown that the efficiency of this dual antimicrobial therapy is highly dependent on the structure of the photosensitizer, being tetrapyrrolic macrocycles the ones with most promising results. There are a few review articles in the recent literature describing the main microbiological results concerning this dual inactivation of bacteria, but none of them focus on the synthetic processes of these photosensitizers and their remarkable chemical versatility. Therefore, herein we present an overview on synthetic methodologies for preparation of tetrapyrrolic macrocycles and their conjugates with antibiotics or antimicrobial peptides, for use in dual inactivation of bacteria. This review will be divided in two sections concerning the physical or covalent combinations of PS with antibiotic/cationic peptides, followed by brief critical analysis on their corresponding antimicrobial outcomes.

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“…The reaction mixture was heated at 60 °C temperature for 12 hours. The progress of the reaction was analyzed by 1 H, 13 C, and 11 B NMR spectroscopic techniques. The yield of each product was calculated by 1 H NMR integration of the characteristic signal of the product in the reaction mixture with 1,3,5-trimethoxybenzene (20 mol %) as the internal standard.…”

Section: Preparation Of Titanium(iv) Amide Complex [{K 2 -C 6 H 4 C(o...mentioning

confidence: 99%

“…Titanium with its highest oxidation state (+IV) is thermodynamically preferred and possesses a high electrostatic potential and therefore exhibits high Lewis acidity [8] . Owing to these properties, titanium compounds have been reported to exhibit exceptional reactivity towards various organic reactions such as Sharpless epoxidations, [9] olefin metathesis, [10] olefinations of carbonyl compounds, [11] Ziegler‐Natta catalysis, [12] condensation reactions, [13] Friedel‐Crafts reactions [14] and Diels‐Alder additions, [15] etc., and toward bond activation reactions like radical reactions, [16] reductive couplings, [17] and stoichiometric dinitrogen activations [18] . However, the oxophillic and moisture‐sensitive nature of titanium complexes limits its potential use as a catalyst for the synthesis of fine chemicals, pharmaceuticals, and agrochemicals in comparison to late transition metal catalysts [19] .…”

Section: Introductionmentioning

confidence: 99%

Efficient Hydroboration of Esters and Nitriles Using a Quinazolinone‐Supported Titanium(IV) Multitasking Catalyst

et al. 2023

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We report catalytic hydroboration of esters as well as nitriles under solvent‐free and mild conditions using single titanium(IV) metal complex, [{κ2‐C6H4C(O)N(iPr)C(N‐iPr)=N}{κ3‐(iPr)N=C(O)−C6H4−NC(NMe2)N(iPr)}TiNMe2] 1 as a sustainable, economical, and efficient pre‐catalyst. The molecular structure of the TiIV complex in the solid state reveals the unique coordination of TiIV metal with N, N, and O atoms of one quinazolinone unit via in‐situ rearrangement, while another quinazolinone moiety coordinates in bidentate fashion via both N atoms only. The TiIV complex demonstrates excellent activity as a pre‐catalyst towards the hydroboration of a wide array of esters and nitriles with pinacolborane (HBpin) to afford alkoxyboranes and diboryl amines in high yield (up to 99 %) with greater tolerance to a variety of electron‐withdrawing and electron‐donating functional groups. A most plausible mechanism of hydroboration of esters is also proposed based on kinetics and NMR studies, which suggests the formation of titanium‐hydride species as an active catalyst.

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Recent advances of carbonyl olefination via McMurry coupling reaction

Abstract: McMurry coupling reaction utilizes the low-valent titanium reagents and carbonyl compounds to produce olefins.

Cited by 25 publications

References 109 publications

Advances in the application of named reactions in polymer synthesis

Advances in the application of named reactions in polymer synthesis

Synthesis of Photosensitizers Based on Tetrapyrrolic Macrocycles for Combination with Antibiotics: Dual Inactivation of Bacteria

Efficient Hydroboration of Esters and Nitriles Using a Quinazolinone‐Supported Titanium(IV) Multitasking Catalyst

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