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Synthesis of Thio‐/Selenopyrrolines via SnCl 4 ‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thio‐/Selenocyanates
Author(s) -
Singh Prasoon Raj,
Kalaramna Pratibha,
Ali Shamsad,
Goswami Avijit
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100846
Subject(s) - chemistry , thio , cycloaddition , moiety , thiocyanate , nitrile , lewis acids and bases , catalysis , chemoselectivity , medicinal chemistry , aryl , organic chemistry , acceptor , alkyl , physics , condensed matter physics
A straightforward protocol has been developed to access thio‐/selenopyrrolines through a (3+2)‐cycloaddition of aryl thio‐/selenocyanates with donor‐acceptor cyclopropanes (DACs) in the presence of SnCl 4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3‐cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)‐cycloaddition reactions.