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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5416-5420
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	29
DOIs	https://doi.org/10.1021/acs.orglett.3c01650
Publication status	Published - 28 Jul 2023

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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.",

author = "Hidekazu Arii and Daisuke Nakane and Kenichi Nakao and Hideki Masuda and Takayuki Kawashima",

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T1 - Dehydrogenative Annulation of Silylated 1H-Indoles with Alkynes via Silyl Migration

AU - Arii, Hidekazu

AU - Nakane, Daisuke

AU - Nakao, Kenichi

AU - Masuda, Hideki

AU - Kawashima, Takayuki

PY - 2023/7/28

Y1 - 2023/7/28

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85166363728

U2 - 10.1021/acs.orglett.3c01650

DO - 10.1021/acs.orglett.3c01650

M3 - Article

C2 - 37449923

AN - SCOPUS:85166363728

SN - 1523-7060

VL - 25

SP - 5416

EP - 5420

JO - Organic Letters

JF - Organic Letters

IS - 29

ER -

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

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