Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

被引：62
|
作者：
Mulina, Olga M. [1 ]
Zhironkina, Nataliya V. [1 ,2 ]
Paveliev, Stanislav A. [1 ]
Demchuk, Dmitry V. [1 ]
Terent'ev, Alexander O. [1 ,2 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninskiy Prospekt, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, 9 Miusskaya Sq, Moscow 125047, Russia
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 05期
基金：
俄罗斯基础研究基金会;
关键词：
O BOND FORMATION; METAL-FREE; ORGANIC ELECTROSYNTHESIS; RADICAL CYCLIZATION; ONE-POT; ARENESULFONOHYDRAZIDES; HYDROGENATION; SULFONAMIDES; ALCOHOLS; ALKENES;
D O I：
10.1021/acs.orglett.0c00139
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N-2 molecule. Furthermore, a formal paradox is observed: a double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.
引用
收藏
页码：1818 / 1824
页数：7
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