2020
DOI: 10.1002/cctc.202001294
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Abstract: A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solven… Show more

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Cited by 12 publications
(18 citation statements)
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“…Recently, we elaborated a facile protocol for the carbonylation of oxetane and thietane to γ‐(thio)butyrolactone by making full use of the dual function of in‐situ generated HCo(CO) 4 as both protonic acid and carbonylation catalyst. (3‐Benzyl)thietane was converted into the corresponding thiobutyrolactone under 30 atm syngas atmosphere at 140 °C [11] . Although no noble metal catalyst is required in above‐mentioned protocols, high pressure of syngas, elevated reaction temperature and limited substrate scope impede its further application.…”
Section: Methodsmentioning
confidence: 99%
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“…Recently, we elaborated a facile protocol for the carbonylation of oxetane and thietane to γ‐(thio)butyrolactone by making full use of the dual function of in‐situ generated HCo(CO) 4 as both protonic acid and carbonylation catalyst. (3‐Benzyl)thietane was converted into the corresponding thiobutyrolactone under 30 atm syngas atmosphere at 140 °C [11] . Although no noble metal catalyst is required in above‐mentioned protocols, high pressure of syngas, elevated reaction temperature and limited substrate scope impede its further application.…”
Section: Methodsmentioning
confidence: 99%
“…Initially, following the reported conditions for the carbonylative ring expansion of oxetane, [11] we tested the carbonylative ring expansion of thietane 1 a using Co 2 (CO) 8 (5 mol%) and dimethoxyethane (DME) as the pre‐catalyst and the solvent under 30 atm pressure of syngas at 100 °C. However, only a small amount of desired thiobutyrolactone 2 a was obtained (Table 1, entry 1).…”
Section: Methodsmentioning
confidence: 99%
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“…A further cascade process by means of an efficient domino relay metathesis sequences using triallyl 3‐oxindole and indole precursors to access fused bicyclic indoxyl dimers and carbazole derivatives is described in the Communication by the Dash group, [10] while a ligand‐ and additive‐free process developed by the Hoover group allows a straightforward aerobic cobalt‐catalyzed synthesis of 2‐aminobenzimidazoles starting from 2‐aminoanilines [11] . An efficient cobalt‐catalyzed carbonylative ring expansion of oxetanes or thietanes under syngas atmosphere route towards γ‐(thio)butyrolactone is presented by the Dong group [12] . The power of ruthenium nanolayers as catalysts for acceptorless dehydrogenative synthesis of quinolones has been demonstrated in the Communication by Chaudhari and Nagaoka [13] .…”
Section: Figurementioning
confidence: 99%
“…[11] An efficient cobalt-catalyzed carbonylative ring expansion of oxetanes or thietanes under syngas atmosphere route towards γ-(thio)butyrolactone is presented by the Dong group. [12] The power of ruthenium nanolayers as catalysts for acceptorless dehydrogenative synthesis of quinolones has been demonstrated in the Communication by Chaudhari and Nagaoka. [13] A bimetallic iridium/ copper catalytic system developed by Zhao and co-workers allows for efficient synthesis of phthalides from readily available benzoic acids and saturated ketones.…”
mentioning
confidence: 98%