The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon-carbon bond formation via electrogenerated N-acyliminium ions

被引:97
作者
Jones, Alan M. [1 ]
Banks, Craig E. [1 ]
机构
[1] Manchester Metropolitan Univ, Fac Sci & Engn, Sch Sci & Environm, Div Chem & Environm Sci, Manchester M1 5GD, Lancs, England
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷
关键词
anodic oxidation; electrochemistry; electroorganic; electrosynthesis; N-acyliminium ions; natural products; non-Kolbe oxidation; peptidomimetics; Shono oxidation; synthesis; SOLID-SUPPORTED BASES; IN-SITU GENERATION; ELECTROLYTIC PARTIAL FLUORINATION; ASSISTED SEQUENTIAL INTRODUCTION; CATIONIC GLYCINE EQUIVALENTS; REVERSE-TURN PEPTIDOMIMETICS; PARALLEL LAMINAR-FLOW; ANODIC-OXIDATION; ELECTROCHEMICAL CYCLIZATION; ORGANIC ELECTROSYNTHESIS;
D O I
10.3762/bjoc.10.323
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-acyliminium ions are useful reactive synthetic intermediates in a variety of important carbon-carbon bond forming and cyclisation strategies in organic chemistry. The advent of an electrochemical anodic oxidation of unfunctionalised amides, more commonly known as the Shono oxidation, has provided a complementary route to the C-H activation of low reactivity intermediates. In this article, containing over 100 references, we highlight the development of the Shono-type oxidations from the original direct electrolysis methods, to the use of electroauxiliaries before arriving at indirect electrolysis methodologies. We also highlight new technologies and techniques applied to this area of electrosynthesis. We conclude with the use of this electrosynthetic approach to challenging syntheses of natural products and other complex structures for biological evaluation discussing recent technological developments in electroorganic techniques and future directions.
引用
收藏
页码:3056 / 3072
页数:17
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