Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant

被引：12

作者：

Kumaraswamy, Gullapalli ^{[1
,2
]}

Vijaykumar, Swargam ^{[1
]}

Ankamma, Kukkadapu ^{[1
]}

Narayanarao, Vykunthapu ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Hyderabad 500607, Telangana, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 48期

关键词：

LASER FLASH-PHOTOLYSIS; DIPHENYL DISELENIDE; ADDITION-REACTIONS; GENERATION; CATALYSIS; PHOTOOXYGENATION; STEREOCHEMISTRY; ACTIVATION; DISULFIDE; CLEAVAGE;

D O I：

10.1039/c6ob02033j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of regio-and stereoselective aryl substituted alpha, beta-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating dissolved oxygen as a chemical switch for two different reaction pathways. The salient feature of this protocol is the single electron transfer (SET) achieved by irradiation of one of two organic molecules thereby avoiding a sensitizer to form a radical ion pair.

引用

页码：11415 / 11425

页数：11

共 44 条

[31] Carbon-Carbon Bond Forming Reactions via Photogenerated Intermediates [J].