Work

Synthesis of Substituted Chromanes and Tetrahydroquinolines via Tandem 1,2-Silyl Shift–Friedel–Crafts Cyclization

Year: 2026

Type: article

Abstract: Propargyl silanes bearing an aryl ether or aniline moiety undergo acid-promoted 1,2-silyl shift to generate an allyl cation, which subsequently alkylates the adjacent aryl group in a Friedel–Crafts fashion. The developed methodology furnishes chromanes in 24–99% yields and 1,2,3,4-tetrahydroquinolines in 21–77% yields, depending on the substitution pattern. The distinctive feature of the developed methodology is the synthesis of (trialkylsilyl)vinyl- and ( Z )-2-halo-1-(trialkylsilyl)vinyl-substituted heterocycles. Propargyl silanes bearing chloro- and bromoalkyne motifs afford cyclization products in higher yields than their terminally unsubstituted alkyne counterparts, providing access to trisubstituted ( Z )-alkenes with high stereoselectivity. The paper also reports an improved protocol for silver-catalyzed haloalkyne synthesis, which is enabled by the use of Ag 2 CO 3 or AgOAc catalysts.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c03136

Authors: Artjoms Ubaidullajevs, Rasma Kroṇkalne, Anatoly Mishnev, Ma̅ris Turks

Institutions: Riga Technical University, Latvijas Organiskās Sintēzes Institūts

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Latvijas Zinātnes Padome, Rīgas Tehniskā Universitāte