Divergent elementoboration: 1,3-haloboration versus 1,1-carboboration of propargyl esters

Wilkins, Lewis C., Soltani, Yashar, Lawson, James R., Slater, Ben and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley: 12 months
ISSN:	0947-6539
Funders:	EPSRC, EPSRC, The University of Padova, The Cassa di Risparmio di Padova e Rovigo Foundation (www.fondazionecariparo.it, Ph.D. studies grant for G.B., LOral Foundation UNESCO (http://www.forwomeninscience.com/en/fellowships, EPSRC
Date of First Compliant Deposit:	24 May 2018
Date of Acceptance:	27 April 2018
Last Modified:	08 May 2023 16:50
URI:	https://orca.cardiff.ac.uk/id/eprint/111706

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