Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates

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 SnCl4 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.

Automated summary

A simple protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition reaction using SnCl4 as a Lewis acid catalyst. Good chemoselectivity was observed when DACs were treated, indicating that thiocyanate is more reactive than nitrile moiety in such reactions.