This work describes the 6-endo-dig cyclization of Saryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing
intramolecular silver-catalyzed alkyne hydroarylation and Niodosuccinimide-promoted iodoarylation. Additionally, a PTSAcatalyzed thiolation reaction of propargylic alcohols was developed
to synthesize the required tertiary S-aryl propargyl ethers. The
applicability of merging these two methods is demonstrated by
synthesizing the retinoic acid receptor antagonist AGN194310.
