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Silver‐Catalyzed Stereoselective trans Addition of 4‐Hydroxycoumarins to Haloalkynes and Late‐Stage Nitration
Author(s) -
Hong Xianfang,
Ma Fang,
Zha Dandan,
Li Hongji
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800625
Subject(s) - nitration , chemistry , stereoselectivity , catalysis , silver nitrate , halide , organic chemistry , oxidative addition , combinatorial chemistry , medicinal chemistry
An efficient silver‐catalyzed stereoselective trans ‐addition of 4‐hydroxycoumarins to haloalkynes under ambient air is described, allowing the straightforward synthesis of vinyl halides. The late‐stage nitration of the resulting products with silver nitrate proceeded with retention of configuration, affording a series of nitroalkenes in good yields. Additionally, DFT calculations were employed for mechanistic studies, and a possible mechanism for the Ag(I)‐catalyzed addition was proposed.