Di‐
            <i>Tert</i>
            ‐Butyl Hyponitrite

Cren, Sylvaine; Renaud, Philippe

doi:10.1002/047084289x.rd062.pub3

Cited by 1 publication

(1 citation statement)

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“…Thus, we decided to pursue the optimization by determining the yields and diastereomeric ratio by GC analysis. Initiation with Et 3 B and di-tert-butyl hyponitrite (DTBHN) [62] at 55 °C proved to be more efficient, 69% yield, and reproducible (Table 1, entry 3). The addition of a substoichiometric amount of K 2 CO 3 (0.3 equivalent) resulted in a slight increase of the yield (Table 1, Entry 4), presumably because it prevented the acidcatalysed decomposition of radical precursor 1 b via HI elimination and deiodination.…”

Section: Optimization and Scope Of The Reactionmentioning

confidence: 99%

Borylated Cyclopentanes via Atom Transfer Radical [3+2] Annulation

Cirule,

Dénès,

Gnägi‐Lux

et al. 2024

Adv Synth Catal

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Abstract. An atom transfer radical [3+2] annulation (ATRAn) reaction involving alkenyl boronic esters and homoallylic iodides provides a rapid access to polysubstituted borylated cyclopentanes. A variety of α‐substituted vinylboronic esters are suitable substrates and offer unique opportunities for further modification of the formed 5‐membered ring. For instance, the oxidation of the boronic ester to an alcohol allows the preparation of products that corresponds to an annulation involving the enol form of acetone. Substitution of the iodide by a nucleophile such as lithium methoxide without modifying the boronic ester moiety is also feasible. Finally, by using a (3‐acetoxyprop‐1‐en‐2‐yl)boronic ester, a facile 1,2‐elimination reaction provided a methylenecyclopentane. In this case, the alkenylboronate radical trap acts as an equivalent to allene, a building block so far elusive for preparative radical reactions.

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Section: Optimization and Scope Of The Reactionmentioning

confidence: 99%