38377-57-0

Upstream product

• 6262-42-6 1,2,3,3-tetrachlorocyclopropene 
• 108-88-3 toluene 
• 675-09-2 4,6-Dimethyl-2-pyron 
• 77902-60-4 C₁₈H₁₇O⁽¹⁺⁾*BF₄^(1-) 
• 886-38-4 diphenylcyclopropenone 
• 70769-70-9 1,3-bis(4-methylphenyl)-2-propanone 
• 67-66-3 chloroform 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 622-47-9 4-tolylacetic acid 
• 104-81-4 4-Methylbenzyl bromide 
• 501034-28-2 1,3-dibromo-1,3-di-p-tolyl-propan-2-one 

Downstream Products

• 73567-97-2 4,4-Dicyan-1,2-bis(p-tolyl)triafulven 
• 77902-60-4 C₁₈H₁₇O⁽¹⁺⁾*BF₄^(1-) 
• 675-09-2 4,6-Dimethyl-2-pyron 
• 886-38-4 diphenylcyclopropenone 
• 73442-24-7 3-Diethylamino-2-phenyl-4,5-di-(p-tolyl)-2,4-cyclopentadien-1-on 
• 28488-78-0 2-(2,3-Di-p-tolyl-cycloprop-2-enylidene)-1-phenyl-butane-1,3-dione 
• 501034-32-8 (4,6-di-p-tolyl-[1,2,3]triazin-5-yl)-diethyl-amine 
• 852063-99-1 2,3-di-p-tolyl-indolizine-7-carbonitrile 
• 852063-68-4 1-bromo-2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile 
• 852063-71-9 toluene-4-sulfonic acid 7-cyano-2,3-di-p-tolyl-indolizin-1-yl ester 

Relevant academic research and scientific papers

Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone

An unprecedented C═C double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.

Lanthanide Silylamide-Catalyzed Synthesis of Pyrano[2,3- b]indol-2-ones

A lanthanide silylamide-catalyzed tandem reaction of isatins, diethyl phosphite, and 2,3-diarylcyclopropenones has been developed. A series of pyrano[2,3-b]indol-2-ones were synthesized in high yields. The cooperation of the Lewis acidity of the lanthanide center and the Bronsted basicity of the N(SiMe3)2 anion may be the key factor affecting the catalytic activity of lanthanide amides.

Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles

Represented is a CuX2- or I2-promoted ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, providing an efficient method for the synthesis of 3-haloacrylates. The ring-opening reaction enables the construction of two C–X (X = Cl, Br, or I) bonds and a C–O bond as well as the cleavage of two C–O bonds and a C–C bond in a single step. This protocol is highly atom economical, has an excellent substrate scope, and exhibits the ability for gram-scale reaction.

Iron-Catalyzed One-Step Synthesis of Isothiazolone/1,2-Selenazolone Derivatives via [3+1+1] Annulation of Cyclopropenones, Anilines, and Elemental Chalcogens

Described herein is the one-step synthesis of isothiazolone/1,2-selenazolone derivatives via [3+1+1] cycloaddition of cyclopropenone derivatives, anilines, and elemental chalcogens. The cascade reaction involves the C?S, C?N, and N?S bond formation along with the cleavage of C?C bond. Both anilines and cyclopropenones are tolerated and give the corresponding products in 28–73% yields. (Figure presented.).

Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides

Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.

Rh(III)-Catalyzed [3 + 3] Annulation Reaction of Cyclopropenones and Sulfoxonium Ylides toward Trisubstituted 2-Pyrones

A new Rh(III)-catalyzed [3 + 3] annulation reaction between cyclopropenones and β-ketosulfoxonium ylides has been reported, enabling metal carbene insertion to access a wide range of trisubstituted 2-pyrones with moderate to excellent yields via C-C single-bond cleavage, in which sulfoxonium ylides serve as potential safe precursors of metal carbenes. This reaction occurred under redox-neutral conditions with a broad substrate scope.

Organocatalytic Regiodivergent C?C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks

Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain-release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen-bonding network activation and a regiodivergent strain-assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a “spring-loaded” intermediate with switchable C?C bond cleavages achieved by controllable ring-strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.

Organocatalyzed [3 + 2] Annulation of Cyclopropenones and β-Ketoesters: An Approach to Substituted Butenolides with a Quaternary Center

An unprecedented organocatalyzed [3 + 2] annulation of cyclopropenones and β-ketoesters has been developed. This reaction provides a direct approach to highly substituted butenolides with a quaternary center in moderate to good yields. The preliminary mechanism study verified that the enol intermediate is crucial to the reaction outcome and the intermolecular esterification and intramolecular Michael addition process were involved.

Development of a catalytic platform for nucleophilic substitution: Cyclopropenone-catalyzed chlorodehydration of alcohols

Cyclopropenone makes the switch: 2,3-Bis-(p-methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium-activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.

Synthesis of 2-methyl-4, 6-diaryl-1, 2, 3-triazinones via diarylcyclopropenones

2-Methyl-4,6-bis(4-substituted-phenyl)-1,2,3-triazin-5(2H)-ones 9a-d were prepared from the coressponding cyclopropenones 4a-d in a similar fashion as described by us previously. One of the the structure of 9b was established by an X-ray analysis.