Photocatalytic intramolecular radical cyclization involved synergistic SET and HAT: synthesis of 3,3-difluoro-γ-lactams
Literature Information
Publication Date
2020-12-16
DOI
10.1039/D0QO01188F
Impact Factor
5.281
Authors
Xiaohui Zhuang, Xiayue Shi, Rui Zhu, Bin Sun
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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2-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide
CAS Number:
1370261-96-3
Molecular Formula:
C19H23N9O
(E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol
CAS Number:
581802-26-8
Molecular Formula:
C11H21BO3
1-(3-Bromo-4-fluorophenyl)methanamine hydrochloride (1:1)
CAS Number:
202865-68-7
Molecular Formula:
C7H8BrClFN
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