Journal
SYNLETT
Volume 32, Issue 9, Pages 905-912Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1468-5962
Keywords
green synthesis; catalyst-free; ligand-free; base-free; radical cyclization; alpha-C(sp(3))-H functionalization
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Funding
- Fundamental Research Funds for the Provincial Universities of Zhejiang [SJLY2021004]
- Zhejiang Provincial Natural Science Foundation of China [LQ19B020004]
- Foundation of Zhejiang Educational Committee [Y201839490]
- Foundation of Wenzhou Basic Scientific Research Project [G20180015]
- Doctoral Fund of Ministry of Education of China (Western Region Postdoctoral Talent Funding Program) [2018M633616XB]
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A new, efficient, and practical radical cyclization of olefinic amides with ketones has been developed for the first time, utilizing alpha-C(sp(3))-H functionalization in the presence of tert-butyl peroxybenzoate (TBPB). The method allows for the synthesis of a wide range of benzoxazines under mild conditions with good to excellent yields and high functional group tolerance.
A new, efficient, and practical radical cyclization of olefinic amides with ketones through alpha-C(sp(3))-H functionalization in the presence of tert-butyl peroxybenzoate (TBPB) is described for the first time. This protocol assembles a wide range of pivotal and useful benzoxazines in good to excellent yields under mild, catalyst-free, ligand-free, and base-free conditions with wide functional group tolerance. Moreover, the mechanistic study indicates that the.-carbonyl radical is involved in this transformation.
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