2009
DOI: 10.1021/jo900396z
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Waste-Free Synthesis of Condensed Heterocyclic Compounds by Rhodium-Catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes

Abstract: The direct oxidative coupling of 2-amino- and 2-hydroxybenzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding 8-substituted isocoumarin derivatives, some of which exhibit solid-state fluorescence. Depending on conditions, 4-ethenylcarbazoles can be synthesized selectively from 2-(arylamino)benzoic acids. The oxidative coupling reactions of heteroarene carboxylic acids as well as aromatic diacids with an alkyne are also … Show more

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Cited by 184 publications
(54 citation statements)
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“…Thus, the aerobic oxidative coupling using a catalyst system of [{RhCl 2 Cp*} 2 ]/Cu(OAc) 2 ⋅ H 2 O proceeds in DMF to afford the corresponding isocoumarins in good to excellent yields (Scheme ). In particular, anthranilic and salicylic acid derivatives smoothly undergo the reaction to produce 8‐amino‐ and 8‐hydroxyisocoumarins,15 which are known to exhibit a broad range of interesting biological and photochemical properties 16…”
Section: Coupling Of Carboxylic Acidsmentioning
confidence: 99%
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“…Thus, the aerobic oxidative coupling using a catalyst system of [{RhCl 2 Cp*} 2 ]/Cu(OAc) 2 ⋅ H 2 O proceeds in DMF to afford the corresponding isocoumarins in good to excellent yields (Scheme ). In particular, anthranilic and salicylic acid derivatives smoothly undergo the reaction to produce 8‐amino‐ and 8‐hydroxyisocoumarins,15 which are known to exhibit a broad range of interesting biological and photochemical properties 16…”
Section: Coupling Of Carboxylic Acidsmentioning
confidence: 99%
“…Besides benzoic and naphthoic acids, heteroarene carboxylic acids and aromatic diacids also undergo oxidative coupling in DMF with diphenylacetylene and 4-octyne, respectively. [15] As shown in Schemes 7 and 8, complicated bi-and tricyclic systems can be constructed effectively through the process. In the reactions of diacids, the use of Ag 2 CO 3 as oxidant is essential.…”
Section: Introductionmentioning
confidence: 99%
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“…[8,9] In this regard, different palladium [10][11][12][13] and rhodium catalysts [14][15][16] have already been used to promote the oxidative alkenylation of heteroarenes with a variety of directing groups, namely, imines, [17,18] amines, [19] and carboxylates. [20,21] Rutheniumcatalyst-directed arylation of unactivated C-H bonds with phenols was reported by Ackermann. [22] Milstein et al pioneered the activation of benzene by using alkyl acrylates.…”
Section: Introductionmentioning
confidence: 96%
“…To the best of our knowledge there have been only two reports dealing with the reaction of benzoic acids with internal alkynes to produce cyclic compounds [34,35].…”
Section: Introductionmentioning
confidence: 99%