Projects per year
Abstract
While radical additions to π-bonds are well established, additions to σ-bonds are far less explored. We have found that electron deficient radicals derived from alkyl iodides under visible light irradiation add to the central strained bond of bicyclobutyl (BCB)-boronate complexes and lead to 1,3-alkyl disubstituted cyclobutyl boronic esters in high yields, with full stereospecificity and high levels of stereoselectivity. Novel cyclobutyl-substituted structures, including peptide and steroid boronic ester derivatives can be accessed. Additionally, although the use of electron-rich alkyl iodides as radical precursors was found to be ineffective, an alternative route involving alkylsulfonylation of the BCB-boronate followed by reductive desulfonylation provided access to simple alkyl substituted cyclobutane products.
Original language | English |
---|---|
Pages (from-to) | 9511-9515 |
Number of pages | 5 |
Journal | Journal of the American Chemical Society |
Volume | 141 |
Issue number | 24 |
Early online date | 29 May 2019 |
DOIs | |
Publication status | Published - 19 Jun 2019 |
Fingerprint
Dive into the research topics of 'Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters'. Together they form a unique fingerprint.Projects
- 2 Finished
-
Mapping Pathways in Photocatalytic Cycles using Ultrafast Spectroscopy
Orr-Ewing, A. J. (Principal Investigator)
1/03/18 → 28/02/21
Project: Research
-
PHOTO-BORAD: Fellowship - Mattia Silvi
Aggarwal, V. K. (Principal Investigator)
1/03/17 → 28/02/19
Project: Research