Vinyl Azides as Radical Acceptors in the Vitamin B12-Catalyzed Synthesis of Unsymmetrical Ketones

被引：28

作者：

Dworakowski, Krzysztof R. ^{[1
]}

Pisarek, Sabina ^{[1
]}

Hassan, Sidra ^{[1
]}

Gryko, Dorota ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 23期

关键词：

HYDROPHOBIC VITAMIN-B-12; GENERATION; CHEMISTRY;

D O I：

10.1021/acs.orglett.1c03321

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under light irradiation vitamin B-12 catalyzes the reaction of vinyl azides with electrophiles to afford unsymmetrical carbonyl compounds in decent yields. Mechanistic studies revealed that alkyl radicals are key intermediates in this transformation.

引用

页码：9068 / 9072

页数：5

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