Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 24, Pages 16222-16236Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02793
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Funding
- Chulabhorn Research Institute (CRI)
- Chulabhorn Graduate Institute (CGI)
- Mahidol University
- Center of Excellence on Environmental Health and Toxicology
- Science & Technology Postgraduate Education and Research Development Office (PERDO)
- Ministry of Education
- Thailand Research Fund (TRF) [RSA6180045]
- Royal Golden Jubilee (RGJ) scholarship program [PHD/0139/2560]
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4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 degrees C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.
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