2019
DOI: 10.1021/acs.orglett.9b01672
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Catalytic Redox Chain Ring Opening of Lactones with Quinones To Synthesize Quinone-Containing Carboxylic Acids

Abstract: Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C–H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes… Show more

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Cited by 12 publications
(6 citation statements)
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“…General structure of lactones A (depicted in Figure 1 ) shows the most important structural features of these molecules. It is important to note the presence of endocyclic ester group in target structure ( Figure 1 ) [ 1 ]. Depending on the mutual position of the hydroxyl and carboxyl groups in the starting hydroxy acid, basic four types of lactones are distinguished: α, β, γ (structure B), δ (structure D ), and ε (structure C ), differing in the size of the cyclic ring ( Figure 1 ).…”
Section: Introductionmentioning
confidence: 99%
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“…General structure of lactones A (depicted in Figure 1 ) shows the most important structural features of these molecules. It is important to note the presence of endocyclic ester group in target structure ( Figure 1 ) [ 1 ]. Depending on the mutual position of the hydroxyl and carboxyl groups in the starting hydroxy acid, basic four types of lactones are distinguished: α, β, γ (structure B), δ (structure D ), and ε (structure C ), differing in the size of the cyclic ring ( Figure 1 ).…”
Section: Introductionmentioning
confidence: 99%
“…Similar stresses, to a slightly lesser extent, are also observed in β-lactones, with four cyclic ring atoms. Compounds with a lactone group containing more than six ring atoms are usually unstable due to the unfavorable interactions associated with the structure of the cyclic system [ 1 , 2 , 3 , 4 ].…”
Section: Introductionmentioning
confidence: 99%
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“…A critical task to achieve this reaction design would be the identification of compatible acid catalysis conditions. Given our group’s long-standing interests in heterocyclic chemistry and Hf-catalysis, we herein would like to report our recent progress in developing a Hf­(OTf) 4 -catalyzed 1,6-conjugate addition reaction of azaarenes to p -QMs (Scheme , part c). Our easily operational protocol was well-tolerated by a wide range of readily available substrates, which should serve as an effective approach toward triarylethane synthesis.…”
Section: Introductionmentioning
confidence: 99%
“…The resulting dihydroanthracene derivative (PAOP–H 2 ) contains two benzylic C–H bonds; thus, it is susceptible to oxidative aromatization toward PAOP . It would be oxidized by the remaining Q to PAOP along with replenished HQ ready for the next cycle of reaction, propagating the redox chain . In an alternatively proposed pathway B, PA–H + may react directly with Q, generating a redox active oxonium ion PAH 2 –Q + as the key intermediate (Scheme b).…”
mentioning
confidence: 99%