Amine organocatalysts for highly -selective chlorination of anilines with sulfuryl chloride

A metal catalyst free approach for regioselective ortho -chlorination of anilines has been developed using a secondary amine as the organocatalyst and sulfuryl chloride as the halogen source under mild conditions. A wide range of substrates were compatible with this catalytic system. In addition, th...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 58; no. 96; pp. 13325 - 13328
Main Authors Wang, Xinzhe, Chen, Zhihuang, Liu, Qingqing, Lin, Wenqing, Xiong, Xiaodong
Format Journal Article
Published 01.12.2022
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Summary:A metal catalyst free approach for regioselective ortho -chlorination of anilines has been developed using a secondary amine as the organocatalyst and sulfuryl chloride as the halogen source under mild conditions. A wide range of substrates were compatible with this catalytic system. In addition, this catalytic protocol has been applied to the efficient synthesis of bioactive compounds and modification of drug derivatives. Further studies indicated that the anionic trichloride species was responsible for the ortho -selectivity. A metal catalyst free approach for regioselective ortho -chlorination of anilines has been developed using a secondary amine as the organocatalyst and sulfuryl chloride as the halogen source under mild conditions.
Bibliography:Electronic supplementary information (ESI) available. CCDC
https://doi.org/10.1039/d2cc05320a
For ESI and crystallographic data in CIF or other electronic format see DOI
2158109
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc05320a