One‐Pot Access to Sulfonyl 2‐Arylnaphthalenes via Wacker Oxidation of Sulfonyl <i>o</i>‐Allylchalcones

In this paper, a high-yield, facile route for the scalable synthesis of sulfonyl 2-aroylbenzofurans via a Bi(OTf) 3 -mediated intermolecular double cyclocondensation of α-sulfonyl o-hydroxyacetophenones with substituted α-hydroxy arylketones under mild open-vessel reaction conditions is described. In the overall reaction, water is generated as the only byproduct. Various metal triflate-promoted reactions and conditions are investigated for the efficient one-pot (4 + 1) annulation reaction.

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“…1). On the other hand, the reaction of 2 x [46] with 3 a did not produce 7 b under the standard conditions (Scheme 7, eq. 2).…”

Section: Resultsmentioning

confidence: 98%

Bi(OTf)₃‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

Chang

Chen

2021

Adv Synth Catal

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One‐Pot Construction of Sulfonyl Benzonorcaradienes

Chang

Lin

2023

Adv Synth Catal

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We report here on a one-pot stereoselective synthesis of strained sulfonyl benzonorcaradienes, which proceeds through base-mediated tandem annulation of o-bis-sulfonylmethyl arenes with diversified chalcones (α,β-unsaturated carbonyls) via intermolecular desulfonylative cyclopropanation, followed by intramolecular condensation. A plausible mechanism is proposed and discussed. The proposed synthetic route forms two carboncarbon single (CÀ C) bonds and one carbon-carbon double (C=C) bond.

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One‐Pot Synthesis of Bis‐sulfonyl Dibenzofurans via K₂CO₃‐Mediated Benzannulation of α‐Sulfonyl o‐Hydroxyacetophenones with 1,4‐Dichloro‐2‐butyne

Chang,

Lee,

Chen

2023

Adv Synth Catal

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A one‐pot synthesis method for functionalized bis‐sulfonyl dibenzofurans was developed under an air atmosphere using potassium carbonate–mediated benzannulation of diversified α‐sulfonyl o‐hydroxyacetophenones with 1,4‐dichloro‐2‐butyne. A plausible mechanism was proposed and discussed. This method provides intermolecular double α‐propargylation, sulfonyl migration, and intramolecular ring‐closure via the formation of one carbon–oxygen single (C–O) bond, one carbon–sulfur single (C–S) bond, and two carbon–carbon (C=C) double bonds.

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One‐Pot Access to Sulfonyl 2‐Arylnaphthalenes via Wacker Oxidation of Sulfonyl o‐Allylchalcones

Cited by 9 publications

References 37 publications

Bi(OTf)₃‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

Bi(OTf)₃‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

One‐Pot Construction of Sulfonyl Benzonorcaradienes

One‐Pot Synthesis of Bis‐sulfonyl Dibenzofurans via K₂CO₃‐Mediated Benzannulation of α‐Sulfonyl o‐Hydroxyacetophenones with 1,4‐Dichloro‐2‐butyne

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One‐Pot Access to Sulfonyl 2‐Arylnaphthalenes via Wacker Oxidation of Sulfonyl o‐Allylchalcones

Cited by 9 publications

References 37 publications

Bi(OTf)3‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

Bi(OTf)3‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

One‐Pot Construction of Sulfonyl Benzonorcaradienes

One‐Pot Synthesis of Bis‐sulfonyl Dibenzofurans via K2CO3‐Mediated Benzannulation of α‐Sulfonyl o‐Hydroxyacetophenones with 1,4‐Dichloro‐2‐butyne

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Bi(OTf)₃‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

Bi(OTf)₃‐Mediated (4+1) Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans

One‐Pot Synthesis of Bis‐sulfonyl Dibenzofurans via K₂CO₃‐Mediated Benzannulation of α‐Sulfonyl o‐Hydroxyacetophenones with 1,4‐Dichloro‐2‐butyne