Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes

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Abstract: The direct synthesis of aryl triflones, that is, trifluoromethanesulfonyl arenes, was achieved through the trifluoromethanesulfonylation of benzynes. The trifluoromethanesulfonyl group, one of the fluorinated functional groups, is a highly electron‐negative and mild lipophilic substituent. Aryl triflones have high potential in the synthesis of bioactive compounds and specialty materials. The treatment of 2‐(trimethylsilyl) aryl trifluoromethanesulfonates with cesium fluoride in the presence of 15‐crown‐5 generated benzynes, which reacted with sodium trifluoromethanesulfinate followed by protonation with tBuOH under heating conditions, provided aryl triflones in moderated to good yields. Both symmetrical and unsymmetrical triflones were nicely accessed under the same reaction conditions. Interestingly, the trifluoromethanesulfonylation of unsymmetrical benzyne precursors proceeded smoothly to furnish corresponding aryl triflones in good yields with good to high regioselectivities. The balance of polarization of electric charge as well as steric hindrance of the benzyne intermediates are central factors to control the outcome of regioselectivity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes ; volume:7 ; number:2 ; year:2018 ; pages:204-211 ; extent:8
ChemistryOpen ; 7, Heft 2 (2018), 204-211 (gesamt 8)

Creator: Sumii, Yuji
Sugita, Yutaka
Tokunaga, Etsuko
Shibata, Norio

DOI: 10.1002/open.201700204

URN: urn:nbn:de:101:1-2022083107461611327262

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Sumii, Yuji
Sugita, Yutaka
Tokunaga, Etsuko
Shibata, Norio

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Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes

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Other Objects (12)

Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling

Synthesis of morphinans through anodic aryl-aryl coupling

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

Synthesis of Aryl Ketones by Coupling of Aryl Bromides with an Acyl Equivalent

Stereoselective Synthesis of α-Aryl Amino Acids

Pd-Catalyzed Synthesis of N-Aryl Indoles

Synthesis of α‐Aryl Acrylamides via Lewis‐Base‐Mediated Aryl/Hydrogen Exchange

Synthesis of Aryl Thiocyanates and Aryl Selenocyanates via Visible‐Light Activation of Arylazo Sulfones

Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

Continuous flow synthesis of α-aryl-α-aminophosphonates

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Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling

Synthesis of morphinans through anodic aryl-aryl coupling

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

Synthesis of Aryl Ketones by Coupling of Aryl Bromides with an Acyl Equivalent

Stereoselective Synthesis of α-Aryl Amino Acids

Pd-Catalyzed Synthesis of N-Aryl Indoles

Synthesis of α‐Aryl Acrylamides via Lewis‐Base‐Mediated Aryl/Hydrogen Exchange

Synthesis of Aryl Thiocyanates and Aryl Selenocyanates via Visible‐Light Activation of Arylazo Sulfones

Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

Continuous flow synthesis of α-aryl-α-aminophosphonates

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Synthesis of Aryl Ketones by Coupling of Aryl Bromides with an Acyl Equivalent

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SYNTHESIS OF NEW ARYL IMIDAZOLE QUINOLINE-2-ONES

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