59151-16-5

Upstream product

• 78585-58-7 2-bromobenzyl-α,α-d2 alcohol 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 54321-62-9 (2-bromophenyl)methanol-d₁ 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 78926-73-5 2-(7'-cyclohepta-1',3',5'-trienyl)benzaldehyde formyl-D₁ ethylene acetal 
• 1323309-12-1 (E)-2-styrylbenzaldehyde-formyl-d1 
• 1323309-15-4 (E)-2-(4-methoxystyryl)benzaldehyde-formyl-d1 
• 1601463-97-1 C₁₀H₇⁽²⁾H 
• 1601464-00-9 2-(2-vinylphenyl)-1,8b-dihydrobiphenylene-d2 
• 1601464-37-2 trimethyl[(2-vinylphenyl)ethynyl]silane-d1 
• 90408-77-8 α-deuterio-1-bromo-2-vinylbenzene 
• 6962-60-3 2-benzyl-benzoic acid methyl ester 
• 78926-71-3 2-(2-bromophenyl)-1,3-dioxolane 
• 1529808-72-7 C₂₄H₂₀⁽²⁾HO₃P 
• 1529808-71-6 C₁₂H₁₁⁽²⁾HO₃ 
• 1529808-70-5 C₁₀H₉⁽²⁾HO₃ 

Relevant academic research and scientific papers

SYNTHESIS OF DEUTERATED ALDEHYDES

Described are methods for preparing a deuterated aldehyde using N-heterocyclic carbene catalysts in a solvent comprising D2O. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions without functionality manipulation.

Br?nsted Acid Catalyzed Oxocarbenium-Olefin Metathesis/Rearrangements of 1H-Isochromene Acetals with Vinyl Diazo Compounds

An oxocarbenium-olefin cross metathesis occurs during Br?nsted acid catalyzed reactions of 1H-isochromene acetals with vinyl diazo compounds. Formally a carbonyl-alkene [2 + 2]-cyclization between isobenzopyrylium ions and the vinyl group of vinyl diazoesters, the retro-[2 + 2] cycloaddition produces a tethered alkene and a vinyl diazonium ion that, upon loss of dinitrogen, undergoes a highly selective carbocationic cascade rearrangements to diverse products whose formation is controlled by reactant substituents. Polysubstituted benzobicyclo[3.3.1]oxocines, benzobicyclo[3.2.2]oxepines, benzobicyclopropane, and naphthalenes are obtained in good to excellent yields and selectivities. Furthermore, isotopic tracer and control experiments shed light on the oxocarbenium-olefin metathesis/rearrangement process as well as on the origin of the interesting substituent-dependent selectivity.

N-Heterocyclic Carbene Catalyzed Deuteration of Aldehydes in D 2 O

An N-heterocyclic carbene (NHC)-catalyzed direct deuteration of aldehydes in a mixed solvent of deuterium oxide (D 2 O) and cyclopentyl methyl ether was established. The present deuteration is possibly initiated by the formation of a Breslow intermediate from the aldehyde and the NHC, with subsequent trapping by D 2 O providing the monodeuterated aldehyde.

Method for preparing deuterated aldehyde compound by using halomethyl compound as raw material

The invention provides a method for preparing deuterated aldehyde compound by using halomethyl compound as a raw material. The method comprises the following steps that in solvent and D2O mixed liquidwith a pyridine compound, the halomethyl compound is added; reaction is performed at 0 to 100 DEG C; then, a nitrosobenzene type compound is added for continuous reaction; finally, reaction liquid issubjected to acidification to obtain a target product. The method has the advantages that the used raw materials are cheap and can be easily obtained; expensive reagents or heavy metal raw materialsare not needed; the reaction conditions are simple; the severe conditions such as high temperature are not needed; the cost of the preparation method is low; the operation is simple; the deuterated rate is high and can reach 97 percent; the target product can be easily purified; the yield is high and reaches up to 95 percent. The substrates used by the method have wide applicability; various deuterated aldehyde compounds can be prepared.

One-Pot Synthesis of Deuterated Aldehydes from Arylmethyl Halides

A facile, one-pot approach for synthesizing deuterated aldehydes from arylmethyl halides was developed using D2O as the deuterium source. The efficient process is realized by a sequence of formation, H/D exchange, and oxidation of pyridinium salt intermediates. The mild and air-compatible reaction conditions enable efficient synthesis of diverse deuterated aldehydes with high deuterium incorporation.

One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields. A cascade process that is triggered by an intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene leads to the formation of 4-substituted cycloocta-2,5-dien-1-ones. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

Dihydrobiphenylenes through ruthenium-catalyzed [2+2+2] cycloadditions of ortho-alkenylarylacetylenes with alkynes

A new synthetic route to dihydrobiphenylenes has been developed. The process involves a mild RuII-catalyzed [2+2+2] dimerization of ortho-alkenylarylacetylenes or its more versatile variant, the Ru-catalyzed [2+2+2] cycloaddition of ortho-ethynylstyrenes with alkynes. Mechanistic aspects of this [2+2+2] cycloaddition are discussed. A new synthetic route to dihydrobiphenylenes involves a mild RuII-catalyzed [2+2+2] dimerization of ortho-alkenylarylacetylenes or its more versatile variant, the Ru-catalyzed [2+2+2] cycloaddition of ortho-ethynylstyrenes with alkynes. The mechanistic aspects of this [2+2+2] cycloaddition are also discussed. Copyright

Domino C-H functionalization reactions of gem-dibromoolefins: Synthesis of N-fused benzo[c]carbazoles

A palladium-catalyzed domino transformation of gem-dibromoolefins leading to novel polycyclic benzo[c]carbazoles is described. A unique feature of the current reaction is the participation of both bromides in C-H functionalization processes. Mechanistic studies were conducted to ascertain the sequence of reaction events, and the results indicate that the (Z)-bromide likely reacts in preference to the (E)-bromide.

AuI-catalyzed intramolecular cyclization of 2-alkenylphenyl carbonyl compounds: Exploring the oxophilic Lewis acidity of AuI species

A AuI-catalyzed intramolecular cyclization reaction of 2-alkenylphenyl carbonyl compounds to afford a variety of indene, indenol, and indanone ring systems was developed. In this process, AuI serves to activate the carbonyl group of β-keto esters, aldehydes, and ketones, preferentially exhibiting oxophilicity in the presence of C-C multiple bonds. Furthermore, β-keto esters could participate as the electrophilic partner in reactions with carbon nucleophile such as alkenes. Copyright

Gold(I)- and Yb(OTf)3-Cocatalyzed rearrangements of epoxy alkynes: Transfer of a carbonyl group in a five-membered carbocycle

We report here the intramolecular reactions between α,β-epoxy ketones and alkynes cocatalyzed by gold(I) and Yb(OTf)3. This new catalytic system based on a combination of gold(I) and Yb (OTf)3 allows facile transformation of epoxy alkynes to give novel indene derivatives in moderate to good yields under mild conditions. Moreover, we describe here the first observation of a transfer of a carbonyl group in a five-membered carbocycle during gold-catalyzed reactions. This proposed mechanism is corroborated by isotope-labeling experiments (D and 13C). Furthermore, the probable role of each catalyst in this interesting domino reaction has been examined by 31P NMR experiments. The utilization of gold catalysts combined with rareearth metal salts offers a new concept for the design of catalyst combinations for domino or cascade reactions.