Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)

Naoyuki Suzuki; Sakura Yasaki; Akito Yasuhara; Takao Sakamoto

doi:10.1248/cpb.51.1170

Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)

Chem Pharm Bull (Tokyo). 2003 Oct;51(10):1170-3. doi: 10.1248/cpb.51.1170.

Authors

Naoyuki Suzuki¹, Sakura Yasaki, Akito Yasuhara, Takao Sakamoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.

PMID: 14519923
DOI: 10.1248/cpb.51.1170

Abstract

The sequential Sonogashira reaction and the cyclization reaction of various 2-iodoanilines and terminal alkynes in the presence of a palladium catalyst and tetrabutylammonium fluoride (TBAF) gave the corresponding 2-substituted indoles in good yields.

MeSH terms

Alkynes / chemical synthesis*
Aniline Compounds / chemical synthesis*
Cyclization
Indoles / chemical synthesis*
Quaternary Ammonium Compounds / chemistry*

Substances

Alkynes
Aniline Compounds
Indoles
Quaternary Ammonium Compounds
tetrabutylammonium
aniline