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Photocatalytic intramolecular radical cyclization involved synergistic SET and HAT: synthesis of 3,3-difluoro-γ-lactams
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-12-16 , DOI: 10.1039/d0qo01188f Xiaohui Zhuang 1, 2, 3, 4 , Xiayue Shi 2, 3, 4, 5 , Rui Zhu 2, 3, 4, 5 , Bin Sun 1, 2, 3, 4 , WeiKe Su 1, 2, 3, 4, 5 , Can Jin 1, 2, 3, 4, 5
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-12-16 , DOI: 10.1039/d0qo01188f Xiaohui Zhuang 1, 2, 3, 4 , Xiayue Shi 2, 3, 4, 5 , Rui Zhu 2, 3, 4, 5 , Bin Sun 1, 2, 3, 4 , WeiKe Su 1, 2, 3, 4, 5 , Can Jin 1, 2, 3, 4, 5
Affiliation
A mild and metal-free protocol for visible-light induced intramolecular radical cyclization of N-allyl(propargyl)-2-bromo-2,2-difluoro-N-arylacetamide has been developed. This strategy showed excellent regioselectivity and simple operation to synthesize 4-substituted 3,3-difluoro-γ-lactams with a broad substrate scope. Moreover, mechanistic studies revealed that this transformation proceeded through a cascade radical-type cyclization and hydrogen atom transfer process with PMDETA as a hydrogen-atom donor.
中文翻译:
光催化分子内自由基环化涉及协同SET和HAT:3,3-二氟-γ-内酰胺的合成
已经开发出一种温和且无金属的方案,用于N-烯丙基(炔丙基)-2-溴-2,2-二氟-N-芳基乙酰胺的可见光诱导的分子内自由基环化。该策略显示出优异的区域选择性和简单的操作,可以合成具有广泛底物范围的4-取代的3,3-二氟-γ-内酰胺。此外,机理研究表明,这种转变是通过级联自由基型环化和氢原子转移过程进行的,其中PMDETA为氢原子供体。
更新日期:2020-12-23
中文翻译:
光催化分子内自由基环化涉及协同SET和HAT:3,3-二氟-γ-内酰胺的合成
已经开发出一种温和且无金属的方案,用于N-烯丙基(炔丙基)-2-溴-2,2-二氟-N-芳基乙酰胺的可见光诱导的分子内自由基环化。该策略显示出优异的区域选择性和简单的操作,可以合成具有广泛底物范围的4-取代的3,3-二氟-γ-内酰胺。此外,机理研究表明,这种转变是通过级联自由基型环化和氢原子转移过程进行的,其中PMDETA为氢原子供体。