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Abstract
Radical reactions have found many applications in carbohydrate chemistry, especially in the construction of carbon–carbon bonds. The formation of carbon–heteroatom bonds has been less intensively studied. This mini-review will summarize the efforts to add heteroatom radicals to unsaturated carbohydrates like endo-glycals. Starting from early examples, developed more than 50 years ago, the importance of such reactions for carbohydrate chemistry and recent applications will be discussed. After a short introduction, the mini-review is divided in sub-chapters according to the heteroatoms halogen, nitrogen, phosphorus, and sulfur. The mechanisms of radical generation by chemical or photochemical processes and the subsequent reactions of the radicals at the 1-position will be discussed. This mini-review cannot cover all aspects of heteroatom-centered radicals in carbohydrate chemistry, but should provide an overview of the various strategies and future perspectives.
Highlights
Radical reactions of carbohydrates are important for chemistry, biology, and medicine
H atom abstraction, whichin iscarbohydrate problematic in generated carbohydrate chemistry with and undergo fragmentations ofalkoxyl the way in which such can befrom added to glycals is groups
Heteroatom radicals been known more than 50 examples years and and has recent developments
Summary
Radical reactions of carbohydrates are important for chemistry, biology, and medicine. To develop efficient radical reactions, it is important to understand the reactivities of the corresponding radicals [12,20,21] Such reactive species can have a nucleophilic or an electrophilic character [22], which controls their addition to alkenes. H atom abstraction, whichin iscarbohydrate problematic in generated carbohydrate chemistry with and undergo fragmentations [30,31], [29]. Since and undergo fast fragmentations [30,31], of phosphorus-, the way in which radicals canradicals be is added glycals is to undergo atom abstraction, this mini-review will focus on the addition of such radicals to halogen atoms, phosphorus-, and phosphorus-, sulfur-centered radicals are less prone to undergo atom unknown. To undergo this this mini-review willoffocus on the addition of such radicals to endo-glycals
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