Greener Friedel‐Crafts Acylation Using Microwave‐Enhanced Reactivity of Bismuth Triflate in the Friedel‐Crafts Benzoylation of Aromatic Compounds with Benzoic Anhydride

Tran, Phuong Hoang; Nguyen, Hai Truong; Hansen, Poul Erik; Lê, Thạch Ngọc

doi:10.1002/slct.201601681

Cited by 8 publications

(4 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bi(OTf) 3 was described as an efficient catalyst for the microwave-assisted solvent-free Friedel-Crafts acylation of benzene derivatives with benzoic anhydride [ 139 ]. The benzoylation readily occurred with a wide variety of aromatics in short reaction times (Scheme 50 ).…”

Section: Synthetic Applications In Homogeneous Systemsmentioning

confidence: 99%

Organic Synthesis Using Environmentally Benign Acid Catalysis

Kokel

Schäfer

Török

2019

COS

View full text Add to dashboard Cite

Recent advances in the application of environmentally benign acid catalysts in organic synthesis are reviewed. The work includes three main parts; (i) description of environmentally benign acid catalysts, (ii) synthesis with heterogeneous and (iii) homogeneous catalysts. The first part provides a brief overview of acid catalysts, both solid acids (metal oxides, zeolites, clays, ion-exchange resins, metal-organic framework based catalysts) and those that are soluble in green solvents (water, alcohols) and at the same time could be regenerated after reactions (metal triflates, heteropoly acids, acidic organocatalysts etc.). The synthesis sections review a broad array of the most common and practical reactions such as Friedel-Crafts and related reactions (acylation, alkylations, hydroxyalkylations, halogenations, nitrations etc.), multicomponent reactions, rearrangements and ring transformations (cyclizations, ring opening). Both the heterogeneous and homogeneous catalytic synthesis parts include an overview of asymmetric acid catalysis with chiral Lewis and Brønsted acids. Although a broad array of catalytic processes are discussed, emphasis is placed on applications with commercially available catalysts as well as those of sustainable nature; thus individual examples are critically reviewed regarding their contribution to sustainable synthesis.

show abstract

Section: Synthetic Applications In Homogeneous Systemsmentioning

confidence: 99%

Organic Synthesis Using Environmentally Benign Acid Catalysis

Kokel

Schäfer

Török

2019

COS

View full text Add to dashboard Cite

show abstract

“…Metal triflates, water-compatible Lewis acids, have increased interest in organic synthesis. − Metal triflates are considered green catalysts for alternative traditional Lewis acids due to their strong Lewis acidity and high tolerance toward water. − Metal triflates can be used with organic solvents or water, and they are easily recycled without a decrease in catalytic activity. − Metal triflate has been known as an effective catalyst for Friedel–Craft transformation in the past 2 decades. ,− While there is the conventional understanding that Lewis acid is a stoichiometric requirement for the reaction and metal cation can fill this role, triflate anion also is crucial. − Currently, our theory study highlights that triflate helps stabilize the acylium and accommodate kinetic accessible pathways in the C–C bond formation process . However, the details of how this species is formed under the support of Lewis acid are still unexplored, especially when extending the list to rare-earth metals.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of Friedel–Crafts Acylation Using Metal Triflate in Deep Eutectic Solvents: An Experimental and Computational Study

Nguyen

et al. 2022

ACS Omega

Self Cite

View full text Add to dashboard Cite

In this paper, we develop a method for Friedel−Crafts acylation using metal triflate in deep eutectic solvents. Various metal triflates were tested and provided good to excellent yields of corresponding ketone products. The density functional theory calculation revealed the metal effects on the formation of active intermediate acylium triflate as well as the acidic condition. The metal triflate in the deep eutectic solvent can be recovered and reused with a little loss in the catalytic activity.

show abstract

“…Traditional synthetic approaches to PAHs involve a multitude of Lewis and Brønsted acid catalyzed S E Ar reactions, , in which the Friedel–Craft acylation plays a major role . Recently, new methodologies based on cooperative catalysis, radical substitution, and, significantly, transition-metal-catalyzed C–H activation have been developed.…”

Section: Introductionmentioning

confidence: 99%

Directedortho-Metalation and Anionicortho-Fries Rearrangement of Polycyclic AromaticO-Carbamates: Regioselective Synthesis of Substituted Chrysenes

et al. 2018

View full text Add to dashboard Cite

A general method for the regioselective synthesis of a series of ortho-substituted chrysenyl N, N-diethyl- O-carbamates by the directed ortho-metalation (D oM) strategy is reported. The starting O-carbamates were prepared from the corresponding chrysenols, available by oxidative photochemical cyclization or directed remote metalation tactics. Chrysen-1-yl and chrysene-3-yl ring site selectivity of directed ortho-metalation (D oM) and anionic ortho-Fries rearrangement (A oF) protocols, with s-BuLi/TMEDA, followed by electrophilic quench using a selection of electrophiles, were observed, leading to new chrysenyl derivatives. 5-Chrysenyl N,N-diethyl- O-carbamate underwent instant A oF rearrangement even at -100 °C to furnish chrysenyl o-hydroxycarboxamide. Iterative D oM reactions were carried out to gain insight into the regioselectivity factors.

show abstract

Greener Friedel‐Crafts Acylation Using Microwave‐Enhanced Reactivity of Bismuth Triflate in the Friedel‐Crafts Benzoylation of Aromatic Compounds with Benzoic Anhydride

Cited by 8 publications

References 36 publications

Organic Synthesis Using Environmentally Benign Acid Catalysis

Organic Synthesis Using Environmentally Benign Acid Catalysis

Mechanism of Friedel–Crafts Acylation Using Metal Triflate in Deep Eutectic Solvents: An Experimental and Computational Study

Directedortho-Metalation and Anionicortho-Fries Rearrangement of Polycyclic AromaticO-Carbamates: Regioselective Synthesis of Substituted Chrysenes

Contact Info

Product

Resources

About