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From Propargylic Alcohols to Substituted Thiochromenes: gem -Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation

2021; American Chemical Society; Volume: 86; Issue: 10 Linguagem: Inglês

10.1021/acs.joc.1c00333

1520-6904

Noelia Velasco, Anisley Suárez, Fernando Martínez, Manuel A. Fernández‐Rodríguez, Roberto Sanz, Samuel Suárez‐Pantiga,

Catalytic C–H Functionalization Methods

This work describes the 6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed 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.