61415-29-0

Upstream product

• 10383-90-1 ⁽¹³⁾C-benzaldehyde 
• 558-13-4 carbon tetrabromide 
• 54522-91-7 [α-13C]-benzyl alcohol 
• 42867-45-8 (dibromomethylene)triphenylphosphorane 

Downstream Products

• 1453089-76-3 phenyl(phenyl-β-[¹³C]-ethynyl)iodonium trifluoroacetate 
• 1453089-77-4 2-phenyl-2/3-[¹³C]-imidazo[1,2-a]pyridine 
• 1453089-79-6 3-phenyl-3-[¹³C]-imidazo[1,2-a]pyridine 
• 1557160-38-9 trimethyl(2-phenyl(2-¹³C)ethynyl)silane 
• 1557159-84-8 2-(phenylethynyl)-2,3-dihydro-1H-indene 
• 1557159-81-5 1-(2-phenylethynyl)-1,2-benziodoxol-3(1H)-one 
• 181470-30-4 phenyl-α-[¹³C]acetylenic triflone 
• 23351-79-3 phenyl-α-[¹³C]-acetylene 

Relevant academic research and scientific papers

Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.

Visible-light-induced chemoselective deboronative alkynylation under biomolecule-compatible conditions

Here, we report a visible-light-induced deboronative alkynylation reaction, which is redox-neutral and works with primary, secondary and tertiary alkyl trifluoroborates or boronic acids to generate aryl, alkyl and silyl substituted alkynes. This reaction is highly chemoselective and performs well on substrates containing alkenes, alkynes, aldehydes, ketones, esters, nitriles, azides, aryl halides, alkyl halides, alcohols, and indoles, with no detectable occurrence of side reactions. The mechanism of this novel C(sp3)-C(sp) bond coupling reaction was investigated by luminescence quenching, radical trapping, on-off light, and 13C-isotopic-labeling experiments. This reaction can be performed in neutral aqueous conditions, and it is compatible with amino acids, nucleosides, oligosaccharides, nucleic acids, proteins, and cell lysates.

Unprecedented regiochemical control in the formation of aryl[1,2-a]imidazopyridines from alkynyliodonium salts: Mechanistic insights

Aryl(alkynyl)iodonium salts have been demonstrated to be valuable precursors to a diverse range of heteroaromatic ring systems including aryl[1,2-a]imidazopyridines. Successful application, using the recently described aryl(alkynyl)iodonium trifluoroacetate salts, is described, highlighting for the first time that the regioselectivity of this process is both counter-ion and concentration dependent. Studies with a carbon-13 labelled substrate established that the reactions of alkynyliodonium salts are highly complex and that multiple mechanistic processes appear to be underway simultaneously.

Mechanistic aspects of the C-H alkynylation reaction of acetylenic triflones. Determination of phenyl versus cyclohexyl migratory aptitude for a vinylidine carbene

13C-2 labeled phenyl ethynyl triflone undergoes regiospecific C-H alkynylation upon reaction with cyclohexane. The 13C label is found to be exclusively adjacent to the phenyl group in the product phenyl cyclohexyl acetylene, consistent with cyclohexyl radical addition at the α-position. Control studies show preferential phenyl migration from a vinylidine carbene, thus excluding the presence of such an intermediate.