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

• 26214-65-3 furan-3-carbonyl chloride 
• 2674-04-6 diphenyl cadmium 
• 110-00-9 furan 
• 93-58-3 benzoic acid methyl ester 
• 2227-79-4 benzenecarbothioamide 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 87453-06-3 tributyl(furan-3-yl)stannane 
• 1708-29-8 2,5-dihydrofuran 
• 488-93-7 3-Furoic acid 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 22037-28-1 3-bromofurane 
• 98-88-4 benzoyl chloride 

Downstream Products

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

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

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.

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.

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.

General Method for the Suzuki-Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature

A general, highly selective method for the room temperature Suzuki-Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary amides in high yields. For the first time, a TON of >1000 has been achieved in amide acyl cross-coupling.

N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N-C(O) Cleavage

Despite recent progress in catalytic cross-coupling technologies, the direct activation of N-alkyl-N-aryl amides has been a challenging transformation. Here, we report the first Suzuki cross-coupling of N-methylamino pyrimidyl amides (MAPA) enabled by the controlled nN → πAr conjugation and the resulting remodeling of the partial double bond character of the amide bond. The new mode of amide activation is suitable for generating acyl-metal intermediates from unactivated primary and secondary amides.

Suzuki-Miyaura Cross-Coupling of N-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N-C Cleavage

The formation of C-C bonds from amides by catalytic activation of the amide bond has been thus far possible by steric distortion. Herein, we report the first example of a general Pd-catalyzed Suzuki-Miyaura cross-coupling of planar amides enabled by the combination of (i) electronic-activation of the amide nitrogen in N-acylpyrroles and pyrazoles and (ii) the use of a versatile Pd-NHC catalysis platform. The origin and selectivity of forming acylmetals, including the role of twist, are discussed.