2015
DOI: 10.1039/c4cs00467a
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Radical aryl migration reactions and synthetic applications

Abstract: Radical aryl migration reactions are of particular interest to the chemical community due to their potential application in radical chemistry and organic synthesis. The neophyl rearrangements used as radical clocks for examining the radical-molecular reactions have been known for decades. The combinations of these migrations with other radical reactions have provided a wide range of novel synthetic methodologies that are complementary to nucleophilic rearrangements. This review will give an overview of various… Show more

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Cited by 318 publications
(120 citation statements)
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References 162 publications
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“…Under standard conditions, 4 underwent activation and radical cyclization to afford a mixture of bicyclic products (46% total yield, shown in eqn (1)). In addition to the expected product 5 (arising from 5- exo -trig cyclization), we observed preferential (2.5 : 1) formation of the 6- endo product 6 , 31 and these data are consistent with the proposed radical nature of the described processes. …”
Section: Resultssupporting
confidence: 87%
“…Under standard conditions, 4 underwent activation and radical cyclization to afford a mixture of bicyclic products (46% total yield, shown in eqn (1)). In addition to the expected product 5 (arising from 5- exo -trig cyclization), we observed preferential (2.5 : 1) formation of the 6- endo product 6 , 31 and these data are consistent with the proposed radical nature of the described processes. …”
Section: Resultssupporting
confidence: 87%
“…This mini-review, focused on the radical version of the Smiles rearrangement, presents recent synthetic achievements, updating the work of Tu on radical aryl migration reactions [17]. We will first present the more widespread sp 3 C-centered radical-promoted Smiles rearrangement, while a second section will be devoted to sp 2 C radical-assisted approaches.…”
Section: Introductionmentioning
confidence: 99%
“…The reaction tolerated aromatic β‐ketoesters with various functional groups on the aromatic ring, including halogens, Me, and OMe, except for those containing 4‐Cl, 4‐Br, and 4‐NO 2 substituents due to dehalogenation and reduction of nitrobenzene, providing the corresponding products in poor yields ( 8‐37 , 8‐38 and 8‐42 ) . Compound 1 i , which bears the strong electron‐withdrawing group 4‐CN, produced a mixture of regioisomers 8‐43 and 8‐43′ in a ratio of 2.5:1 and 59 % combined yield, which suggests a radical mechanism involving ipso cyclization followed by rearrangement through the C−C bond cleavage in the spirocyclohexadienyl radical . When a methyl group was introduced to the meta position of the phenyl ring, a mixture of regioisomers 8‐44 and 8‐44′ were obtained in a ratio of 2.9:1 and 65 % combined yield.…”
Section: Methodsmentioning
confidence: 97%