ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Divergent Elementoboration: 1,3-Haloboration versus 1,1-Carboboration of Propargyl Esters.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Transition-Metal-Free Thioboration of Terminal Alkynes.JACS Au · 2024Article
- Reactions of Diethylazo-Dicarboxylate with Frustrated Lewis Pairs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Piers' Borane-Induced Tetramerization of Arylacetylenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Haloboration: scope, mechanism and utility.New journal of chemistry = Nouveau journal de chimie · 2021Review
- Divergent Elementoboration: 1,3-Haloboration versus 1,1-Carboboration of Propargyl Esters.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
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Authors and funding
5 authors.
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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.
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