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

Noelia Velasco | Zendy; Anisley Suárez | Zendy; Fernando Martínez | Zendy; Manuel A. FernándezRodríguez | Zendy; Roberto Sanz | Zendy; Samuel SuárezPantiga | Zendy

Open Access

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

Author(s) -

Noelia Velasco,

Anisley Suárez,

Fernando Martínez,

Manuel A. FernándezRodríguez,

Roberto Sanz,

Samuel SuárezPantiga

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00333

Subject(s) - alkyne , chemistry , propargyl , intramolecular force , aryl , catalysis , medicinal chemistry , combinatorial chemistry , propargyl alcohol , stereochemistry , organic chemistry , alkyl

This work describes the 6- endo - dig cyclization of S -aryl propargyl sulfides to afford 2 H -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.

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