Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations

被引：44

作者：

Kovacs, Szabolcs ^{[1
]}

Bayarmagnai, Bilguun ^{[1
]}

Aillerie, Alexandre ^{[1
]}

Goossen, Lukas J. ^{[1
]}

机构：

[1] Ruhr Univ Bochum, Fak Chem & Biochem, Univ Str 150, D-44801 Bochum, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 10期

关键词：

Phosphorothiolation; sulfur; phosphorus; reagents; copper; Sandmeyer reaction; S-P(O) BOND CONSTRUCTION; S-ARYL PHOSPHOROTHIOATES; ORGANOPHOSPHORUS COMPOUNDS; ARENEDIAZONIUM SALTS; TRIALKYL PHOSPHITES; DIALKYL PHOSPHITES; ORGANIC DISULFIDES; MILD CONDITIONS; P(O)H COMPOUNDS; H-PHOSPHONATES;

D O I：

10.1002/adsc.201701549

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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 Me3SiP(O)(OMe)(2), elemental sulfur and Me4NF. 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.

引用

页码：1913 / 1918

页数：6

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