Ligand‐Promoted RhIII‐Catalyzed Thiolation of Benzamides with a Broad Disulfide Scope

A ligand‐promoted RhIII‐catalyzed C(sp2)−H activation/thiolation of benzamides has been developed. Using bidentate mono‐N‐protected amino acid ligands led to the first example of RhIII‐catalyzed aryl thiolation reactions directed by weakly coordinating directing amide groups. The reaction tolerates...

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Published inAngewandte Chemie International Edition Vol. 58; no. 27; pp. 9099 - 9103
Main Authors Kang, Yan‐Shang, Zhang, Ping, Li, Min‐Yan, Chen, You‐Ke, Xu, Hua‐Jin, Zhao, Jing, Sun, Wei‐Yin, Yu, Jin‐Quan, Lu, Yi
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.07.2019
EditionInternational ed. in English
Subjects
Amides
Amino acids
Aromatic compounds
Chemical reactions
directing groups
disulfides
Ligands
Reagents
rhodium
thiolation
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Summary:A ligand‐promoted RhIII‐catalyzed C(sp2)−H activation/thiolation of benzamides has been developed. Using bidentate mono‐N‐protected amino acid ligands led to the first example of RhIII‐catalyzed aryl thiolation reactions directed by weakly coordinating directing amide groups. The reaction tolerates a broad range of amides and disulfide reagents. Strength from weakness: A ligand‐promoted RhIII‐catalyzed C(sp2)−H activation/thiolation of benzamides has been developed. Using bidentate mono‐N‐protected amino acid ligands led to the first example of RhIII‐catalyzed aryl thiolation reactions directed by weakly coordinating directing amide groups. The reaction tolerates a broad range of amides and disulfide reagents.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201903511