Iridium(I)-catalyzed direct C-H bond alkylation of the C-7 position of indolines with alkenes

Shiguang Pan; Naoto Ryu; Takanori Shibata

doi:10.1002/adsc.201300917

Iridium(I)-catalyzed direct C-H bond alkylation of the C-7 position of indolines with alkenes

Shiguang Pan, Naoto Ryu, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

85 Citations (Scopus)

Abstract

A cationic iridium-catalyzed C-7 alkylation of N-substituted indoline derivatives with various alkenes has been developed. A variety of 7-alkylindolines were obtained in moderate to high yields. This protocol relies on the use of the carbonyl group on the nitrogen atom of indoline as a directing group and it is potentially applicable to the large-scale synthesis of 7-alkylindoles.

Original language	English
Pages (from-to)	929-933
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	5
DOIs	https://doi.org/10.1002/adsc.201300917
Publication status	Published - 2014 Mar 24

Keywords

C-H functionalization
N-substituted indolines
alkenes
alkylation
iridium catalysts

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201300917

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abstract = "A cationic iridium-catalyzed C-7 alkylation of N-substituted indoline derivatives with various alkenes has been developed. A variety of 7-alkylindolines were obtained in moderate to high yields. This protocol relies on the use of the carbonyl group on the nitrogen atom of indoline as a directing group and it is potentially applicable to the large-scale synthesis of 7-alkylindoles.",

keywords = "C-H functionalization, N-substituted indolines, alkenes, alkylation, iridium catalysts",

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AU - Ryu, Naoto

AU - Shibata, Takanori

PY - 2014/3/24

Y1 - 2014/3/24

N2 - A cationic iridium-catalyzed C-7 alkylation of N-substituted indoline derivatives with various alkenes has been developed. A variety of 7-alkylindolines were obtained in moderate to high yields. This protocol relies on the use of the carbonyl group on the nitrogen atom of indoline as a directing group and it is potentially applicable to the large-scale synthesis of 7-alkylindoles.

AB - A cationic iridium-catalyzed C-7 alkylation of N-substituted indoline derivatives with various alkenes has been developed. A variety of 7-alkylindolines were obtained in moderate to high yields. This protocol relies on the use of the carbonyl group on the nitrogen atom of indoline as a directing group and it is potentially applicable to the large-scale synthesis of 7-alkylindoles.

KW - C-H functionalization

KW - N-substituted indolines

KW - alkenes

KW - alkylation

KW - iridium catalysts

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Iridium(I)-catalyzed direct C-H bond alkylation of the C-7 position of indolines with alkenes

Abstract

Keywords

ASJC Scopus subject areas

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