Access to γ-Iodo-gem-Diborylated Cyclopentanes and to Bicyclic Cyclopropanes
Publisher DOI
Abstract
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. Furthermore, this work highlights that 1,1-diborylethene represents a synthetic equivalent to ketene, a so far elusive radical trap due to its daunting reactivity.
Date Issued
2024-07-02
Publication Type
Article
Subject(s)
Language(s)
en
Journal
Advanced Synthesis & Catalysis
Publisher
Wiley
ISSN
1615-4150
1615-4169
Access(Rights)
open.access