α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

被引：52
|
作者：
Caiuby, Clarice A. D. [1 ]
de Jesus, Matheus P. [1 ]
Burtoloso, Antonio C. B. [1 ]
机构：
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 11期
基金：
巴西圣保罗研究基金会;
关键词：
HIGHLY SUBSTITUTED PYRROLES; DIAZO OXIME ETHERS; C-H ANNULATION; TITANIUM TETRACHLORIDE; ASYMMETRIC-SYNTHESIS; OXOSULFONIUM YLIDES; EXPEDIENT SYNTHESIS; DIVERGENT SYNTHESIS; CATALYZED REACTIONS; ORGANIC-SYNTHESIS;
D O I：
10.1021/acs.joc.0c00833
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate alpha-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl](2) (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding beta-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
引用
收藏
页码：7433 / 7445
页数：13
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