1557159-81-5

Upstream product

• 10383-90-1 ⁽¹³⁾C-benzaldehyde 
• 61415-29-0 1,1-dibromo-2-[¹³C]-styrene 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 1557160-38-9 trimethyl(2-phenyl(2-¹³C)ethynyl)silane 
• 10383-88-7 acetophenone-13C=O 
• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 71-43-2 benzene 
• 88-67-5 2-Iodobenzoic acid 

Downstream Products

• 1557159-84-8 2-(phenylethynyl)-2,3-dihydro-1H-indene 

Relevant academic research and scientific papers

Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols

Ethynylbenziodoxol(on)es (EBXs) have been widely used in organic synthesis as electrophilic alkyne-transfer reagents involving carbon- and heteroatom-based nucleophiles. However, potential reactions of EBXs with phenols remain uninvestigated. Here, we present the formation of (Z)-2-iodovinyl phenyl ethers with excellent regio- and stereoselectivity through the reactivity between EBXs and phenols driven by visible light. We propose that this light-activated transformation proceeds through electron donor-acceptor complexes to enable new reactivity beyond existing mechanisms for alkynylation of carbon- and heteroatom-based nucleophiles. This operationally robust process was employed for the synthesis of diverse (Z)-2-iodovinyl phenyl ethers through irradiating a solution containing a phenyl-EBX, a phenol, and the base Cs2CO3 with a commercially available blue LED at room temperature. The (Z)-2-iodovinyl phenyl ether products can be further stereospecifically functionalized to form trisubstituted alkenes, demonstrating the potential of these products en route to chemical complexity.

Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations

The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)-C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.

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.

Palladium-catalyzed condensation of N -aryl imines and alkynylbenziodoxolones to form multisubstituted furans

A palladium(II) catalyst promotes condensation of an N-aryl imine and an alkynylbenziodoxolone derivative to afford a multisubstituted furan, whose substituents are derived from the alkynyl moiety (2-position), the imine (3- and 4-positions), and the 2-iodobenzoate moiety (5-position), along with an N-arylformamide under mild conditions. The 2-iodophenyl group of the furan product serves as a versatile handle for further transformations. A series of isotope-labeling experiments shed light on the bond reorganization process in this unusual condensation reaction, which includes cleavage of the C-C triple bond and fragmentation of the carboxylate moiety.

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.