HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF3-indenes and DFT study of intermediate carbocations

Selbi K Nursahedova; Aleksey V Zerov; Irina A Boyarskaya; Elena V Grinenko; Valentine G Nenajdenko; Aleksander V Vasilyev

doi:10.1039/c8ob02887g

HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF₃-indenes and DFT study of intermediate carbocations

Org Biomol Chem. 2019 Jan 31;17(5):1215-1224. doi: 10.1039/c8ob02887g.

Authors

Selbi K Nursahedova¹, Aleksey V Zerov, Irina A Boyarskaya, Elena V Grinenko, Valentine G Nenajdenko, Aleksander V Vasilyev

Affiliation

¹ Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, 194021, Russia. aleksvasil@mail.ru a.vasilyev@spbu.ru.

PMID: 30652720
DOI: 10.1039/c8ob02887g

Abstract

The reaction of CF3-propargyl alcohols [ArC[triple bond, length as m-dash]CCH(OH)CF3] with arenes under the action of acidic HUSY zeolite CBV-720 was investigated. It was found that the reaction at 100 °C for 1 h gave rise to 3-aryl-1-CF3-indenes in up to 83% yield. Electronic characteristics of the reaction key intermediates, mesomeric CF3-propargyl-allenyl cations [ArC[triple bond, length as m-dash]C-HC+(CF3) ↔ ArC+[double bond, length as m-dash]C[double bond, length as m-dash]CH(CF3)], were studied by DFT calculations. A plausible cationic reaction mechanism is discussed.

Publication types

Research Support, Non-U.S. Gov't