Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

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Abstract: The radical Truce–Smiles rearrangement is a straightforward strategy for incorporating aryl groups into organic molecules for which asymmetric processes remains rare. By employing a readily available and non‐expensive chiral auxiliary, we developed a highly efficient asymmetric photocatalytic acyl and alkyl radical Truce–Smiles rearrangement of α‐substituted acrylamides using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom–transfer photocatalyst, along with aldehydes or C−H containing precursors. The rearranged products exhibited excellent diastereoselectivities (7: 1 to >98: 2 d.r.) and chiral auxiliary was easily removed. Mechanistic studies allowed understanding the transformation in which density functional theory (DFT) calculations provided insights into the stereochemistry‐determining step.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides ; day:06 ; month:08 ; year:2024 ; extent:10
Angewandte Chemie / International edition. International edition ; (06.08.2024) (gesamt 10)

Creator: Ma, Wei‐Yang
Leone, Matteo
Derat, Etienne
Retailleau, Pascal
Reddy, Chada Raji
Neuville, Luc
Masson, Géraldine

DOI: 10.1002/anie.202408154

URN: urn:nbn:de:101:1-2408071424124.843587021613

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

Last update: 14.08.2025, 10:53 AM CEST

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Associated

Ma, Wei‐Yang
Leone, Matteo
Derat, Etienne
Retailleau, Pascal
Reddy, Chada Raji
Neuville, Luc
Masson, Géraldine

Other Objects (12)

Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 3-TRIFLUOROMETHYL-7-ALKOXY-9-NITROPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 3-TRIFLUOROMETHYL-7-ALKOXY-9-NITROPHENOTHIAZINES VIA SMILES REARRANGEMENT

Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 3-TRIFLUOROMETHYL-7-ALKOXY-9-NITROPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 3-TRIFLUOROMETHYL-7-ALKOXY-9-NITROPHENOTHIAZINES VIA SMILES REARRANGEMENT

Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

Photocatalytic Asymmetric Acyl Radical Truce–Smiles Rearrangement for the Synthesis of Enantioenriched α‐Aryl Amides

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 3-TRIFLUOROMETHYL-7-ALKOXY-9-NITROPHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF 3-TRIFLUOROMETHYL-7-ALKOXY-9-NITROPHENOTHIAZINES VIA SMILES REARRANGEMENT

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