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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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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Abstract 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.
AbstractList 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.
Author Lin, Wenqing
Liu, Qingqing
Chen, Zhihuang
Wang, Xinzhe
Xiong, Xiaodong
AuthorAffiliation School of Pharmacy
Nanchang University
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  surname: Lin
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– sequence: 5
  givenname: Xiaodong
  surname: Xiong
  fullname: Xiong, Xiaodong
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Notes 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
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Snippet A metal catalyst free approach for regioselective ortho -chlorination of anilines has been developed using a secondary amine as the organocatalyst and sulfuryl...
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Title Amine organocatalysts for highly -selective chlorination of anilines with sulfuryl chloride
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