Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations. Issue 10 (26th March 2018)

• Record Type: Journal Article
• Authors: Kovács, Szabolcs; Bayarmagnai, Bilguun; Aillerie, Alexandre; Gooßen, Lukas J.
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 10(2018)
• Page Start: 1913
• Page End: 1918
• Publication Date: 2018-03-26
• Subjects: Phosphorothiolation -- sulfur -- phosphorus -- reagents -- copper -- Sandmeyer reaction; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701549
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: New late‐stage phosphorothiolation methods are disclosed that allow the efficient transfer of SP(O)(OR)2 groups to diversely functionalized substrates using nucleophilic and electrophilic reagents. The nucleophilic reagent, tetramethylammonium O, O ‐dimethyl phosphorothioate, was synthesized in near‐quantitative yield from Me3 SiP(O)(OMe)2, elemental sulfur and Me4 NF. Its umpolung with N ‐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. Abstract :