Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles

An alternative entry to transformations of <i>N</i>-sulfonyl-4-(2-(ethynyl)­aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically, the reaction is proposed to involve a key silver carbenoid intermediate, thus enabling the formation of multiple chemical bonds via ring opening, N₂ extrusion, silver carbenoid formation, nucleophilic addition, and complex annulations cascades

[4 + 2] Annulation Cascades of 2‑Bromo-1-arylpropan-1-ones with Terminal Alkynes Involving C–Br/C–H Functionalization

Straightforward access to various substituted naphthalenones by copper-catalyzed [4 + 2] annulation cascades of 2-bromo-1-arylpropan-1-ones with terminal alkynes is presented. Employing a Cu­(MeCN)₄PF₄ catalyst and 1,10-phenanthroline (1,10-Phen) ligand enables the formation of three new C–C bonds in a single reaction via [4 + 2] annulation of a 2-bromo-1-arylpropan-1-one with an alkyne followed by α-alkylation with the other 2-bromo-1-arylpropan-1-one with excellent functional group tolerance and step efficiency

Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles

An alternative entry to transformations of <i>N</i>-sulfonyl-4-(2-(ethynyl)­aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically, the reaction is proposed to involve a key silver carbenoid intermediate, thus enabling the formation of multiple chemical bonds via ring opening, N₂ extrusion, silver carbenoid formation, nucleophilic addition, and complex annulations cascades

Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles

An alternative entry to transformations of <i>N</i>-sulfonyl-4-(2-(ethynyl)­aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically, the reaction is proposed to involve a key silver carbenoid intermediate, thus enabling the formation of multiple chemical bonds via ring opening, N₂ extrusion, silver carbenoid formation, nucleophilic addition, and complex annulations cascades

Copper-Catalyzed Radical [2 + 2 + 1] Annulation of Benzene-Linked 1,<i>n</i>‑Enynes with Azide: Fused Pyrroline Compounds

A novel selective copper-catalyzed radical [2 + 2 + 1] annulation of benzene-linked 1,<i>n</i>-enynes with azido-benziodoxolone to access fused pyrroline compounds, including 3<i>H</i>-pyrrolo­[3,4-<i>c</i>]­quinolin-4­(3<i>aH</i>)-ones, chromeno­[3,4-<i>c</i>]­pyrrol-4­(9<i>bH</i>)-one, and indeno­[1,2-<i>c</i>]­pyrroline, has been developed, which proceeds via the addition of the azide radical to the alkene, annualtion, and azidation cascade

Metal-Free Oxidative <i>Ipso</i>-Carboacylation of Alkynes: Synthesis of 3‑Acylspiro[4,5]trienones from <i>N</i>‑Arylpropiolamides and Aldehydes

A general and metal-free radical route to synthesis of 3-acylspiro­[4,5]­trienones is established that utilizes TBHP (<i>tert</i>-butyl hydrogenperoxide) as an oxidation and a reaction partner to trigger the oxidative <i>ipso</i>-carboacylation of <i>N</i>-arylpropiolamides with aldehydes. This method offers a new difunctionalization of alkynes through oxidative cross coupling of the aldehyde C­(sp²)–H bond with an <i>ipso</i>-aromatic carbon

Manganese-Catalyzed Intermolecular Oxidative Annulation of Alkynes with γ‑Vinyl Aldehydes: An Entry to Bridged Carbocyclic Systems

Manganese-catalyzed intermolecular oxidative annulation of alkynes with γ-vinyl aldehydes involving acylation and alkylation is described, thus providing a scenario for the divergent synthesis of bridged carbocyclic systems. By means of this manganese-catalyzed alkyne dicarbofunctionalization strategy, three chemical bonds, including two C–C bonds and one C–H bond, are formed via an aldehyde C­(sp²)–H oxidative functionalization/[4 + 2] annulation/protonation cascade

1,2-Alkylarylation of Styrenes with α‑Carbonyl Alkyl Bromides and Indoles Using Visible-Light Catalysis

A new intermolecular 1,2-alkylarylation of styrenes with α-carbonyl alkyl bromides and indoles using <i>fac</i>-[Ir­(ppy)₃] as the photoredox catalyst has been developed. The method allows the simultaneous formation of two new carbon–carbon bonds through three component reaction, and represents a new single-electron transfer (SET) strategy for the 1,2-alkylarylation of the styrenes with broad substrate scope and excellent functional group tolerance