Literature DB >> 31415048

A practical copper-catalyzed approach to β-lactams via radical carboamination of alkenyl carbonyl compounds.

Peng Shi1, Jie Wang, Zixu Gan, Jingyu Zhang, Runsheng Zeng, Yingsheng Zhao.   

Abstract

Functionalized β-lactams are highly important motifs in synthetic chemistry. We report an efficient and novel approach to the synthesis of β-lactams via a copper(i)-catalyzed cascade process involving C(benzyl)-H radical abstraction, intermolecular alkene addition, and intramolecular amination reaction. Variously substituted alkenes were synthesized from vinylacetic acid, leading to the corresponding β-lactams in moderate to good yields. Preliminary studies indicate that the reaction undergoes a free radical mechanism via a Cu(i)/Cu(ii)/Cu(iii) catalytic cycle.

Entities:  

Year:  2019        PMID: 31415048     DOI: 10.1039/c9cc05668h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

1.  Modular synthesis of non-conjugated N-(quinolin-8-yl) alkenyl amides via cross-metathesis.

Authors:  Hui-Qi Ni; Zi-Qi Li; Van T Tran; Keary M Engle
Journal:  Tetrahedron       Date:  2021-06-12       Impact factor: 2.388

2.  Copper(i)-catalyzed radical carboamination reaction of 8-aminoquinoline-oriented buteneamides with chloroform: synthesis of-β-lactams.

Authors:  Zixu Gan; Ke Zhang; Peng Shi; Yingsheng Zhao; Runsheng Zeng
Journal:  RSC Adv       Date:  2021-08-19       Impact factor: 4.036

3.  Copper-catalyzed aerobic oxidative radical alkoxycyclization of tryptamines to access 3-alkoxypyrroloindolines.

Authors:  Wei Wang; Jun-Rong Song; Zhi-Yao Li; Ting Zhong; Qin Chi; Hai Ren; Wei-Dong Pan
Journal:  RSC Adv       Date:  2021-05-19       Impact factor: 4.036

  3 in total

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