Abstract
AbstractNew late‐stage phosphorothiolation methods are disclosed that allow the efficient transfer of SP(O)(OR)2groups to diversely functionalized substrates using nucleophilic and electrophilic reagents. The nucleophilic reagent, tetramethylammoniumO,O‐dimethyl phosphorothioate, was synthesized in near‐quantitative yield from Me3SiP(O)(OMe)2, elemental sulfur and Me4NF. Its umpolung withN‐bromophthalimide provided the electrophilic reagent,O,O‐dimethyl‐S‐(N‐phthalimido)phosphorothioate. Complementary methods based on these reagents enable the phosphorothiolation of diversely functionalized alkyl halides, arenediazonium salts, arylboronic acids and electron‐rich arenes in good yields under mild conditions.magnified image
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