Regioselective double vicinal carbon-carbon bond forming reactions of electron-deficient alkenes by use of allylic stannanes and organoiodo compounds

Free‐Radical‐Mediated Multicomponent Coupling Reactions

“…Because of the nucleophilic nature of ordinary alkyl radicals, the addition of an alkyl radical to tributylallyltin is not very fast, yet fast enough to transfer the radical chain [28]. This is an advantage for the controlled O Scheme 6.14 sequential alkene addition reactions shown in Scheme 6.15, which shows two examples of tin radical three-component coupling reactions using a mixture of alkyl halides, electron-deficient alkenes and allyltin [29]. The reactions are conducted with a mixture of two alkenes.…”

Free-radical Carbo-functionalization of Olefins Using Sulfonyl Derivatives

“…1,4-Addition of nucleophilic species onto α,β-unsaturated enones and enoates, followed by the trapping of the resulting enolate with an external electrophile constitutes a useful process in organic synthesis, which has seen many developments in the field of natural product synthesis. [7] A radical version was developed earlier by Mizuno, Otsuji and co-workers, [8] using allylstannanes as final allylic trap. Similarly to its ionic counterpart, remarkable examples of diastereo-and enantioselective radical carbo-allylation have been reported using allylstannanes.…”

Radical and Radical–Ionic Multicomponent Processes

“…[19] Mizuno, Otsuji, and coworkers were the first to develop a radical version of this process. [20] Nucleophilic radical (e.g., 20 i) generated from iodides such as 20 efficiently adds to electron-poor olefins 21 in a 1,4-fashion (Scheme 8). This leads to a new electron-deficient radical intermediate 21 i, which can be allylated with stannane 22, to afford 23 in moderate to excellent yields, along with a tributyltin radical that sustains the radical chain.…”