Unlocking copper catalysis with nitro compounds: Synthesis of functionalized allylboranes from allylic nitroalkanes

05 April 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A copper-catalyzed borylation of allylic nitroalkanes is reported. The method, which exploits the high versatility of the nitroalkane precursors, tolerates a variety of functional groups and allows a straightforward access to diversely substituted allylboronic esters in high yields. This unprecedented reactivity towards copper complexes has been further exploited in the synthesis of a number of γ fluoroallyl boronic esters starting from readily available α fluoroallyl nitroalkanes, as well as in various post-functionalizations towards synthetically useful building blocks. Both the reaction mechanism and the chemoselectivity have been rationalized experimentally and through DFT calculations.


Copper catalysis
Allylboronic esters
Fluoroallyl boronic esters

Supplementary materials

Supporting Information
The Supporting Information contains details of DFT protocols, synthetic procedures and characterization data


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