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Divergent Elementoboration: 1,3-Haloboration versus 1,1-Carboboration of Propargyl Esters.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 May 23; Vol. 24 (29), pp. 7364-7368. Date of Electronic Publication: 2018 Apr 27. - Publication Year :
- 2018
-
Abstract
- This work showcases the 1,3-haloboration reaction of alkynes in which boron and chlorine add to propargyl systems in a proposed sequential oxazoliumborate formation with subsequent ring-opening and chloride migration. In addition, the functionalization of these propargyl esters with dimethyl groups in the propargylic position leads to stark differences in reactivity whereby a formal 1,1-carboboration prevails to give the 2,2-dichloro-3,4-dihydrodioxaborinine products as an intramolecular chelate. Density functional theory calculations are used to rationalize the distinct carboboration and haloboration pathways. Significantly, this method represents a metal-free route to highly functionalized compounds in a single step to give structurally complex products.<br /> (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 24
- Issue :
- 29
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 29700863
- Full Text :
- https://doi.org/10.1002/chem.201801493