Dehydrogenative Annulation of Silylated 1 H-Indoles with Alkynes via Silyl Migration

Hidekazu Arii; Daisuke Nakane; Kenichi Nakao; Hideki Masuda; Takayuki Kawashima

doi:10.1021/acs.orglett.3c01650

Dehydrogenative Annulation of Silylated 1 H-Indoles with Alkynes via Silyl Migration

Org Lett. 2023 Jul 28;25(29):5416-5420. doi: 10.1021/acs.orglett.3c01650. Epub 2023 Jul 14.

Authors

Hidekazu Arii¹, Daisuke Nakane², Kenichi Nakao², Hideki Masuda², Takayuki Kawashima³

Affiliations

¹ Faculty of Education, University of Miyazaki, 1-1 Gakuen Kibanadai Nishi, Miyazaki 889-2192, Japan.
² Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.
³ Graduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Gunma, Japan.

PMID: 37449923
DOI: 10.1021/acs.orglett.3c01650

Abstract

We investigated the dehydrogenative annulation of silylated 1H-indole derivatives with alkynes to synthesize a silole-fused indole. The addition of the in situ generated silylium ion to alkynes was followed by the sila-Friedel-Crafts reaction via silyl migration, realizing regioselective dehydrogenative annulation controlled by the steric bulkiness of a base. The optical properties of the obtained siloloindoles indicated fluorescence of which the intensity depends on the location of the fused silole.