Easy Access to γ-Iodo-gem-Diborylated-Cyclopentanes and Bicyclic Cyclopropanes

25 January 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A formal atom transfer radical [3+2] annulation (ATRAn) reaction between different homoallyl radical precursors and 1,1-diborylethene was developed. It provides a rapid access to polysubstituted cyclopentanes containing a gem-diboronic ester moiety. The synthetic utility of theses uniquely functionalized 5-membered rings is highlighted by their easy conversion to attractive borylated building blocks such as 1-borylated bicyclo[3.1.0]hexanes. The ATRAn reaction was extended to homopropagylic radicals giving access to unique allylic gem-diboronic esters that could be used in allylboration of aldehydes.


radical reaction
gem-diboronic esters
iodine atom transfer

Supplementary materials

Experimental part
Experimental procedures, product characterizations, and copies of NMR spectra


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