Copper-Catalyzed Carboamination of Unactivated Alkenes to Synthesize β-Lactams with Trichloroacetonitrile

被引:0
|
作者
Wang, Xiaoya [1 ]
Cui, Jing [1 ]
Zeng, Runsheng [1 ]
机构
[1] Scoohow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou, Peoples R China
关键词
beta-Lactam; copper catalyst; dichlorocyanomethyl; radical reaction; STEREOSELECTIVE-SYNTHESIS; INTRAMOLECULAR AMINATION; C(SP(3))-H; AMIDATION; CARBOXAMIDES; CYCLIZATION; ACTIVATION; NITRILES; BONDS;
D O I
10.1002/jhet.4928
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Lactams, as nitrogen-containing heterocycles with distinctive biological activities, have made significant contributions to the treatment of infectious diseases. This study which used inexpensive copper salts as catalysts, trichloroacetonitrile as a radical precursor, and potassium carbonate as base offers a concise route for the synthesis of beta-lactam compounds substituted with potentially pharmacologically active dichloroacetyl moieties. Preliminary mechanistic studies indicate that unactivated alkenes undergo sequential intermolecular radical addition and intramolecular amidation reactions. The copper salts undergo catalytic cycles involving Cu(I)/Cu(II)/Cu(III) species.
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页数:8
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