6453-98-1

Usage

Safety Profile

A poison by intraperitoneal route. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating vapors.

InChI:InChI=1/C11H8O2/c12-8-9-3-1-4-10(7-9)11-5-2-6-13-11/h1-8H

Upstream product

• 110-00-9 furan 
• 100-47-0 benzonitrile 
• 1708-29-8 2,5-dihydrofuran 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 488-93-7 3-Furoic acid 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 26214-65-3 furan-3-carbonyl chloride 
• 98-88-4 benzoyl chloride 
• 55552-70-0 furan-3-boronic acid 
• 5145-65-3 N-benzoylpyrrole 
• 55-21-0 benzamide 
• 6343-27-7 1-benzoylpyrrolidine-2,5-dione 

Downstream Products

• 1428339-05-2 3-((4-(tert-butyl)phenyl)(phenyl)methyl)furan 
• 1428362-14-4 C₁₈H₁₆N₂O₃S 
• 104919-84-8 4-Benzoyl-5-hydroxy-5H-furan-2-one 
• 104919-77-9 Phenyl-(2,3,7-trioxa-bicyclo[2.2.1]hept-5-en-5-yl)-methanone 
• 102029-10-7 [3]furyl-phenyl ketone-(4-phenyl semicarbazone) 

Relevant academic research and scientific papers

Destannylative acylation of 1-[(2-methoxyethoxy)methoxy]-2- (phenylsulfonyl)-2-(tributylstannyl)cyclopropane: A novel route to 3- acylfurans

Destannylative acylation of 1-[(2-methoxyethoxy)methoxy]-2- (phenylsulfonyl)-2-(tributylstannyl)cyclopropane (1) provided dihydrofurans 5 in good yields, which upon treatment with BF3.OEt2 in CH2Cl2 led to the formation of 3-acylfurans 6 in moderate yields. The reaction was proposed to proceed via the intramolecular Prins-type reaction of the oxonium intermediate 7.

Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage

Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe

N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by Nlpto Ar Conjugation Switch

The development of new amide precursors for selective, catalytic activation of carbon-nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki-Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N-C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.

Palladium-Catalyzed Amide N-C Hiyama Cross-Coupling: Synthesis of Ketones

N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a broad substrate scope and showed good functional group tolerance. N-Benzoylsuccinimide and N-protected N-phenylbenzamides showed good activities in coupling reactions with phenylsiloxane. The employment of CuF2 as an activor afforded the decarbonylative products at 160 °C.

Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP

An efficient and user-friendly palladium(II) precatalyst, POxAP (post-oxidative-addition precatalyst), was identified for use in Fukuyama cross-coupling reactions. Suitable for storage under air, the POxAP precatalyst allowed reaction between thioesters and organozinc reagents with turnover numbers of ～90000. A series of 23 ketones were obtained with yields ranging from 53 to 99%. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin.

Pd-PEPPSI: Water-Assisted Suzuki?Miyaura Cross-Coupling of Aryl Esters at Room Temperature using a Practical Palladium-NHC (NHC=N-Heterocyclic Carbene) Precatalyst

A Pd-PEPPSI-catalyzed (Pd=Palladium, PEPPSI=pyridine-enhanced precatalyst preparation stabilization and initiation) Suzuki-Miyaura cross-coupling of aryl esters via selective C?O cleavage at room temperature is reported. The developed catalyst system displays broad substrate scope with respect to both components under practical ambient reaction conditions using readily-available, cheap, modular, air- and moisture-stable Pd-NHC precatalyst (NHC=N-heterocyclic carbene). The use of water proved crucial for achieving high reactivity in this coupling. The catalyst system represents the mildest conditions for the Suzuki?Miyaura cross-coupling of aryl esters reported to date. The protocol also allowed for achieving TON >1,000 (TON=turnover number) in the Suzuki?Miyaura ester coupling for the first time. (Figure presented.).

Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters

Esters are valuable electrophiles for cross-coupling due to their ubiquity and ease of synthesis. However, harsh conditions are traditionally required for the effective cross-coupling of ester substrates. Utilizing a recently discovered precatalyst, Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of the C(acyl)-O bond of aryl esters that proceed under mild conditions are reported. The Pd(II) precatalyst is highly active because it is reduced to the Pd(0) active species more rapidly than previous precatalysts.

Palladium-catalyzed Suzuki-Miyaura coupling of aryl esters

The Suzuki-Miyaura coupling is among the most important C-C bond-forming reactions available due to its reliability, chemoselectivity, and diversity. Aryl halides and pseudohalides such as iodides, bromides, and triflates are traditionally used as the electrophilic coupling partner. The expansion of the reaction scope to nontraditional electrophiles is an ongoing challenge to enable an even greater number of useful products to be made from simple starting materials. Herein, we present how an NHC-based Pd catalyst can enable Suzuki-Miyaura coupling where the C(acyl)-0 bond of aryl esters takes on the role of electrophile, allowing the synthesis of various ketone-containing products. This contrasts known reactions of similar esters that provide biaryls via nickel catalysis. The underlying cause of this mechanistic divergence is investigated by DFT calculations, and the robustness of esters compared to more electrophilic acylative coupling partners is analyzed.

Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.

Pd-PEPPSI: A General Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling of Esters by C-O Cleavage

The Suzuki-Miyaura cross-coupling of aryl esters by selective C-O bond cleavage represents a powerful methodology in organic synthesis. Here, we report that versatile, easily prepared, well-defined Pd-PEPPSI type precatalysts serve as highly reactive catalysts for the direct Suzuki-Miyaura cross-coupling of esters. Sterically and electronically diverse aryl esters couple with arylboronic acids in good to excellent yields using a single, operationally simple protocol. Kinetic studies demonstrate that the cross-coupling of aryl esters proceeds with rates similar to the cross-coupling of amides. This study strongly supports the use of well-defined Pd(II)-NHC precatalysts bearing pyridine throw-away ligands for the selective C(acyl) cleavage of bench-stable carboxylic acid derivatives. Considering the modular scaffold of Pd-NHC precatalysts, we envision that the method will be of general interest for the development of new catalysts for C-O cleavage reactions.