Carbofunctionalization of Terminal Alkynes via Rhodium Catalysis Enabling Formations of Four Different Bonds.

Described here is the oxygenative carbofunctionalization of terminal alkynes mediated by combined rhodium catalysis that enables regioselective quadruple formation of C-C, C-H, C-O, and C-heteroatom bonds. Mechanistic studies suggest that a disubstituted rhodium vinylidene complex is generated upon C-C bond formation at the terminal alkyne with tethered electrophiles such as alkyl halides, aldehydes, imines, and Michael acceptors. Subsequent intermolecular transfer oxygenation of the rhodium vinylidene with pyridine N-oxide generates a rhodium-complexed ketene intermediate that reacts with a variety of heteroatom nucleophiles to give rise to cyclic carboxylic acid derivatives.

• Publication year

  2023

• Venue

  Organic Letters

• Publication date

  2023-03-17

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.3c00341PMID 36930814
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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