Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants

被引：7

作者：

Nasrallah, Ali ^{[1
]}

Grelier, Gwendal ^{[1
]}

Lapuh, Maria Ivana ^{[1
,2
,3
]}

Duran, Fernando J. ^{[2
,3
]}

Darses, Benjamin ^{[1
]}

Dauban, Philippe ^{[1
]}

机构：

[1] Univ Paris Saclay, Inst Chim Subst Nat, CNRS UPR 2301, Univ Paris Sud, 1 Av Terrasse, F-91198 Gif Sur Yvette, France

[2] Univ Buenos Aires, Dept Quim Organ, Fac Ciencias Exactas & Nat, CONICET, Buenos Aires, DF, Argentina

[3] Univ Buenos Aires, UMYMFOR, Fac Ciencias Exactas & Nat, CONICET, Buenos Aires, DF, Argentina

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 42期

关键词：

Hypervalent Iodine; Rhodium; Epoxidation; Alkenes; Lewis acids; C-H AMINATION; TERT-BUTYL HYDROPEROXIDE; OXYGEN-ATOM TRANSFER; ORGANIC-SYNTHESIS; INTERMOLECULAR AMINATION; DIRHODIUM CAPROLACTAMATE; DIAZO-COMPOUNDS; OXIDATION; CATALYST; BONDS;

D O I：

10.1002/ejoc.201800306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh-2(tpa)(4) (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)(2) is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent.

引用

页码：5836 / 5842

页数：7

共 97 条

[1] Asymmetric formal synthesis of (-)-pancracine via catalytic enantioselective C-H amination process [J].