Synthesis of Acyl Terphenyls and Higher Polyaromatics via Base-Promoted C-H Functionalization of Acetylarenes with Arylacetylenes

Elena Yu Schmidt; Elena V Ivanova; Inna V Tatarinova; Igor' A Ushakov; Nadezhda V Semenova; Alexander V Vashchenko; Boris A Trofimov

doi:10.1021/acs.orglett.6b00782

Synthesis of Acyl Terphenyls and Higher Polyaromatics via Base-Promoted C-H Functionalization of Acetylarenes with Arylacetylenes

Org Lett. 2016 May 6;18(9):2158-61. doi: 10.1021/acs.orglett.6b00782. Epub 2016 Apr 25.

Authors

Elena Yu Schmidt¹, Elena V Ivanova¹, Inna V Tatarinova¹, Igor' A Ushakov¹, Nadezhda V Semenova¹, Alexander V Vashchenko¹, Boris A Trofimov¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str., 664033 Irkutsk, Russia.

PMID: 27110838
DOI: 10.1021/acs.orglett.6b00782

Abstract

KO(t)Bu/DMSO-promoted C-H functionalization of acetylarenes with arylacetylenes (100 °C, 30 min), generating β,γ-ethylenic ketones, triggers upon further heating (100 °C, 4 h, with or without acidifying additive) the cascade assembly of acyl terphenyls and higher polyaromatics in good yields.

Publication types

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