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Different Performances of BF 3 , BCl 3 , and BBr 3 in Hypervalent Iodine-Catalyzed Halogenations.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2023 Apr 07; Vol. 88 (7), pp. 4359-4371. Date of Electronic Publication: 2023 Mar 20. - Publication Year :
- 2023
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Abstract
- Herein, hypervalent iodine-catalyzed halogenation of aryl-activated alkenes using BX <subscript>3</subscript> (X = Cl, Br) as the halogen source and activating reagents was reported. Various halogenated 1,3-oxazine/2-oxazoline derivatives were obtained in good-to-high yields. Using BF <subscript>3</subscript> resulted in different substitute sites from BBr <subscript>3</subscript> and BCl <subscript>3</subscript> of the products, indicating different reactive intermediates and reaction pathways. The reaction underwent a "ligand coupling/oxidative addition/intermolecular nucleophilic attack/1,2-aryl migration/reductive elimination/intramolecular nucleophilic attack" cascade when BF <subscript>3</subscript> was applied as the halogen source, while 1,2-aryl migration has "disappeared" when the halogen source was BBr <subscript>3</subscript> or BCl <subscript>3</subscript> . Possible catalytic cycles were proposed, and DFT calculations were conducted to demonstrate the differences among BX <subscript>3</subscript> (X = F, Cl, Br) in the hypervalent iodine-catalyzed halogenations.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 88
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 36939669
- Full Text :
- https://doi.org/10.1021/acs.joc.2c02967