Journal
ORGANIC LETTERS
Volume 23, Issue 14, Pages 5329-5333Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01599
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Funding
- National Natural Science Foundation of China [21676076, 21725602, 21878071, 21971060]
- Natural Science Foundation of Changsha [kq2004008]
- HuXiang High Talent of Hunan Province [2018RS3042]
- Recruitment Program for Foreign Experts of China [WQ20164300353]
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A mild method for N-acylation of primary and secondary amines with alpha-diketones induced by ultraviolet (UV) light was developed in this study. The system showed high yields of products with various functional groups at room temperature. Mechanistic studies revealed the in-situ generation of benzoin from benzil under UV irradiation.
Herein, we develop a mild method for N-acylation of primary and secondary amines with alpha-diketones induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350-380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under UV irradiation.
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