Sulfide-Directed Ir-Catalyzed Vinylic sp 2 and Benzylic sp 3 C-H Activation for the Construction of Sulfur-Containing Medium-Ring System.
Takanori ShibataTakahiro IwakiHaru MarumoMamoru ItoPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2023)
Ir-catalyzed transformations initiated by sulfur-directed vinylic sp 2 and benzylic sp 3 C-H activation are disclosed that achieve the construction of sulfur-containing seven- and eight-membered systems. Allyl 2-alkynylphenyl sulfides were transformed into dihydrobenzothiepines in 30-95 % yield, and 2-alkynylaryl 2-tolyl sulfides were converted into dibenzo[b,f]thiepines in 57-95 % yield along with double bond isomerization. In both reactions, the combination of Ir catalyst and sulfide moiety was a key to the facile cyclization.