Convergent Strategy for the Synthesis of Oxa-, Thia-, and Selena[5]helicenes by Acetylene-Activated SNAr Reactions

Samuel M Hoenig; Youmian Yan; Emily A Dougherty; Reuben Hudson; Sava Petovic; Christopher K Lee; Yusheng Hu; Lucas S Gomez; Jeffrey L Katz

doi:10.1021/acs.joc.0c00052

Convergent Strategy for the Synthesis of Oxa-, Thia-, and Selena[5]helicenes by Acetylene-Activated S_NAr Reactions

J Org Chem. 2020 Mar 20;85(6):4553-4559. doi: 10.1021/acs.joc.0c00052. Epub 2020 Mar 12.

Authors

Samuel M Hoenig¹, Youmian Yan¹, Emily A Dougherty¹, Reuben Hudson¹, Sava Petovic¹, Christopher K Lee¹, Yusheng Hu¹, Lucas S Gomez¹, Jeffrey L Katz¹

Affiliation

¹ Department of Chemistry, Colby College, 5754 Mayflower Hill, Waterville, Maine 04901, United States.

PMID: 32133863
DOI: 10.1021/acs.joc.0c00052

Abstract

A tandem acetylene-activated S_NAr-anionic cyclization strategy is presented for the synthesis of chalcogen-containing hetero[5]helicenes. Oxa-, thia-, and selena[5]helicenes are accessed from common ortho-fluoro-ethynylarene precursors, allowing the heteroatoms to be installed at the 1-position or 1- and 12-positions of the hetero[5]helicene inner core surface.

Publication types

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