Wilkins, LC;
Soltani, Y;
Lawson, JR;
Slater, B;
Melen, RL;
(2018)
Divergent Elementoboration: 1,3-Haloboration versus 1,1-Carboboration of Propargyl Esters.
Chemistry - A European Journal
, 24
(29)
pp. 7364-7368.
10.1002/chem.201801493.
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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.
| Type: | Article |
|---|---|
| Title: | Divergent Elementoboration: 1,3-Haloboration versus 1,1-Carboboration of Propargyl Esters |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/chem.201801493 |
| Publisher version: | https://doi.org/10.1002/chem.201801493 |
| Language: | English |
| Additional information: | This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
| Keywords: | Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, Chemistry, alkynes, boranes, boron, haloboration, Lewis acid, FRUSTRATED LEWIS PAIRS, HALOBORATION REACTION, HOMOALLYLIC ALCOHOLS, TERMINAL ALKYNES, ALLYL-BORON, CYCLIZATION, B(C6F5)(3), ALKENES, HYDROGENATION, HYDROBORATION |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10052953 |
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