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2H-Chromene-3-carboxylic Acid Synthesis via Solvent-Controlled and Rhodium(III)-Catalyzed Redox-Neutral C–H Activation/[3 + 3] Annulation Cascade
- Source :
- Organic Letters. 20:3892-3896
- Publication Year :
- 2018
- Publisher :
- American Chemical Society (ACS), 2018.
-
Abstract
- An efficient and redox-neutral synthesis of 2 H-chromene-3-carboxylic acids from N-phenoxyacetamides and methyleneoxetanones has been realized via a solvent-controlled and rhodium(III)-catalyzed C-H activation/unusual [3 + 3] annulation sequence. This transformation represents the first example of using an α-methylene-β-lactone unit as the three-carbon source in transition-metal-catalyzed C-H activations through selective alkyl C-O bond cleavage. Synthetic applications and mechanistic details, including further derivatization of 2 H-chromene-3-carboxylic acids, the isolation and identification of a five-membered rhodacycle, as well as the theoretical studies for reasoning a plausible Rh(III)-Rh(V)-Rh(III) process, have also been discussed.
- Subjects :
- chemistry.chemical_classification
Annulation
010405 organic chemistry
Organic Chemistry
chemistry.chemical_element
010402 general chemistry
01 natural sciences
Biochemistry
Redox
Medicinal chemistry
0104 chemical sciences
Catalysis
Rhodium
Solvent
chemistry.chemical_compound
chemistry
Physical and Theoretical Chemistry
Derivatization
Alkyl
Bond cleavage
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 20
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....12196e08db405bd1feece6e0996cba60