Title: Divergent Elementoboration: 1,3‐Haloboration versus 1,1‐Carboboration of Propargyl Esters

Citation
Wilkins LC, Soltani Y, Lawson JR, et al. (2018). Divergent Elementoboration: 1,3‐Haloboration versus 1,1‐Carboboration of Propargyl Esters. Cardiff University. https://doi.org/10.17035/d.2020.0098717132

Dataset Details

Publisher: Cardiff University

Date (year) of data becoming publicly available: 2018

Coverage start date: 01/01/2014

Coverage end date: 01/04/2018

Data format: .pdf, .cif, .jpg

Software Required: Mercury or similar to view Xray structures

Estimated total storage size of dataset: Less than 100 megabytes

DOI : 10.17035/d.2020.0098717132

DOI URL: http://doi.org/10.17035/d.2020.0098717132

Description

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.

Data includes experimental procedures, X-ray data and NMR spectra.

Research results based upon these data are published at http://doi.org/10.1002/chem.201801493