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Palladium‐Catalyzed [2+2+1] Spiroannulation via Alkyne‐Directed Remote C−H Arylation and Subsequent Arene Dearomatization
- Source :
- Angewandte Chemie International Edition. 59:653-657
- Publication Year :
- 2020
- Publisher :
- Wiley, 2020.
-
Abstract
- Palladium-catalyzed alkene-directed cross-coupling of aryl iodide with another aryl halide through C-H arylation opens a unique avenue for unsymmetrical biaryl-derived molecules. However, homo-coupling of aryl iodides often erodes the overall synthetic efficiency. Reported herein is a highly chemoselective Pd0 -catalyzed alkyne-directed cross-coupling of aryl iodides with bromophenols, which was subsequently followed by phenol dearomatization to furnish a very attractive [2+2+1] spiroannulation. Notably, possible homo-coupling of aryl iodides was not observed at all. Mechanistic studies indicated that a five-membered aryl/vinyl palladacycle most likely accounts for promoting the key step of biaryl cross-coupling.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Aryl halide
Aryl
Iodide
chemistry.chemical_element
Alkyne
General Medicine
General Chemistry
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
chemistry.chemical_compound
chemistry
Molecule
Phenol
Palladium
Subjects
Details
- ISSN :
- 15213773 and 14337851
- Volume :
- 59
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....3f411162fdca7f706cd31c43d32faf93