1,2-Silyl Shift – Ritter Reaction Cascade for the Synthesis of Dihydroisoquinolines and Allylamine Derivatives

International Symposium on Synthesis and Catalysis (ISySyCat 2025): Book of Abstracts 2025
Raimonds Rogaļevs, Sandra Turka, Rasma Kroņkalne, Artjoms Ubaidullajevs, Mikus Puriņš, Māris Turks

1,3-Difunctionalizations are far less common in organic synthesis than their 1,2- and 1,4-counterparts. Propargyl silanes can act as precursors of 1,3-dipols, if their electrophilic activation is followed by 1,2-silyl shift, which generates carbocation or its equivalent. The latter undergoes a proton loss to provide a stable final product if no nucleophile is present in the reaction mixture. However, in the presence of standard O- or S-nucleophiles allyl (thio)ethers and (thio)esters are formed. Herein, we report a development of cascade methodology, which profits from the vinyl cation - allyl cation rearrangement via 1,2-silyl shift.

Keywords
Ritter-type reaction, propargylsilanes, 1,2-silyl shift, allyl amide, dihydroisoquinoline
Hyperlink
https://isysycat2025.events.chemistry.pt/book-of-abstracts

Rogaļevs, R., Turka, S., Kroņkalne, R., Ubaidullajevs, A., Puriņš, M., Turks, M. 1,2-Silyl Shift – Ritter Reaction Cascade for the Synthesis of Dihydroisoquinolines and Allylamine Derivatives. In: International Symposium on Synthesis and Catalysis (ISySyCat 2025): Book of Abstracts, Portugal, Coimbra, 2-5 September, 2025. Coimbra: 2025, pp.200-200.

Publication language
English (en)