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Cu-Mediated Sulfonyl Radical-Enabled 5-exo-trig Cyclization of Alkenyl Aldehydes: Access to Sulfonylmethyl 1H-Indenes
10.1021/acs.joc.8b00341 2018-04-06 An efficient method for the construction of sulfonylmethyl 1H-indenes via Cu(I)-mediated sulfonyl radical-enabled 5-exo-trig cyclization of alkenyl aldehydes has been developed for the first time. Mechanistic studies indicated that a radical addition–cyclizat... |
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Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters
10.1021/acs.joc.8b00447 2018-04-05 A Cu-catalyzed multicomponent cascade reaction of DABCO·(SO2)2 (DABSO), alcohol, and aryl diazonium tetrafluoroborate was developed which afforded sulfonic esters in moderate to good chemical yields. In this reaction, the SO2 surrogate DABSO was used for the ... |
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Synthesis and Self-Aggregation of π-Expanded Chlorophyll Derivatives to Construct Light-Harvesting Antenna Models
10.1021/acs.joc.7b03212 2018-04-05 Chlorosomes are one of the elegant light-harvesting antenna systems in anoxygenic photosynthetic bacteria, whose core is constructed from J-type self-aggregation of bacteriochlorophyll-c, bacteriochlorophyll-d, bacteriochlorophyll-e, and bacteriochlorophyll-f... |
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Phosphine-Free and Reusable Palladium Nanoparticles-Catalyzed Domino Strategy: Synthesis of Indanone Derivatives
10.1021/acs.joc.8b00463 2018-04-05 The carbene migratory insertion involving a domino reaction by highly stable, reusable, and binaphthyl-stabilized Pd-nanoparticles (Pd-BNP) is disclosed. The reaction was catalyzed by 2 mol % of a heterogeneous Pd-BNP catalyst under external ligand-free condi... |
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Copper(I)-Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Azidoformates and Aryl Terminal Alkynes
10.1021/acs.joc.8b00022 2018-04-05 The copper(I)-catalyzed azide–alkyne cycloaddition reaction has been extensively studied and widely applied in organic synthesis. However, the formation of 1,2,3-triazoles with electron-deficient azide has been a challenging problem. In this report, we have d... |
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Classical Example of Total Kinetic and Thermodynamic Control: The Diels–Alder Reaction between DMAD and Bis-furyl Dienes
10.1021/acs.joc.8b00336 2018-04-04 A rare example of chemospecificity in the tandem Diels–Alder reaction of activated alkynes and bis-dienes has been revealed. The reaction between bis-furyl dienes and DMAD occurs at 25–80 °C and leads to kinetically controlled “pincer” adducts, 4a,8a-disubsti... |
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Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds
10.1021/acs.joc.8b00484 2018-04-04 Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Brønsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway... |
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Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles
10.1021/acs.joc.8b00541 2018-04-04 The Lewis acid-promoted phosphorylation of 2-indolylmethanols with diarylphosphine oxides is described. The regioselectivity of the reaction can be modulated by the choice of rare earth metal Lewis acid, offering a highly selective approach to structurally di... |
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Development of a Synthetic Method for Multifunctionalized Pyrroles Using Isocyanide Dichloride as a Key Intermediate
10.1021/acs.joc.8b00185 2018-04-04 Multifunctionalized pyrrole derivatives were synthesized using a highly efficient method based on the Michael addition of carbanions generated in situ from isocyanide dichloride to α,β-unsaturated carbonyl compounds. The reactions proceeded smoothly to afford... |
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Intramolecular Aryne-Furan Cycloadditions for the Synthesis of Anticancer Naphthalimides
10.1021/acs.joc.8b00531 2018-04-04 An intramolecular aryne Diels–Alder reaction with a furan moiety was applied to the synthesis of dihydrobenzo[de]isochromenes as intermediates toward naphthalimides. After oxidation, this method offers an efficient approach for the synthesis of substituted na... |