2016
DOI: 10.1002/chem.201600432
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Brønsted Acid‐Mediated Hydrative Arylation of Unactivated Alkynes

Abstract: The Brønsted acid-mediated reaction of unactivated alkynes with aryl sulfoxides leads to simultaneous hydration and intermolecular C-C bond formation. This solvent- and metal-free transformation directly delivers α-arylated carbonyl compounds as the products of a formal hydrative arylation in an atom-economical manner. The products bear useful synthetic handles for further functionalization.

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Cited by 89 publications
(23 citation statements)
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“…Using a 1:1 mixture of p ‐chloro‐ and p ‐methyl‐arylated sulfoxides, a strong (77:23) preference for the most electron‐rich sulfoxide was observed (Scheme a), akin to the intramolecular case where a sulfoxide carrying both groups was used (Scheme b). These results are consistent with the selectivity previously observed for this type of rearrangement …”
Section: Methodssupporting
confidence: 93%
“…Using a 1:1 mixture of p ‐chloro‐ and p ‐methyl‐arylated sulfoxides, a strong (77:23) preference for the most electron‐rich sulfoxide was observed (Scheme a), akin to the intramolecular case where a sulfoxide carrying both groups was used (Scheme b). These results are consistent with the selectivity previously observed for this type of rearrangement …”
Section: Methodssupporting
confidence: 93%
“…Recently, we34353637383940 and others41424344454647484950515253545556 reported the metal-free, sulfoxide directed57 C–H functionalization of a variety of molecular scaffolds, which was enabled by an interrupted Pummerer reaction28. Spurred on by these recent achievements, we considered the use of benzothiophene S -oxides 1 for the synthesis of important C3-functionalized benzothiophenes, as the corresponding sulfonium salts I and II , formed after reaction with the coupling partners, lack aromaticity about the five-membered ring and should therefore undergo facile C–C bond formation via [3,3]-sigmatropic rearrangement58, thus delivering unexplored reactivity not accessible in benzothiophenes.…”
Section: Resultsmentioning
confidence: 99%
“…Eine 1:1 Mischung aus p ‐Chlor‐ und p ‐Methylarylierten Sulfoxiden zeigte eine starke (77:23) Präferenz für das elektronenreichere Sulfoxid (Schema a) ähnlich zu dem intramolekularen Fall, in dem ein Sulfoxid, das beide Gruppen trägt verwendet wurde (Schema b). Diese Ergebnisse stimmen mit den bisher beobachteten Selektivitäten für diese Art Umlagerung überein …”
Section: Methodsunclassified