Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes

Ltaru Nakamura; Tetsuya Nemoto; Naozumi Shiraiwa; Masahiro Terada

doi:10.1021/ol900113f

Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes

Ltaru Nakamura, Tetsuya Nemoto, Naozumi Shiraiwa, Masahiro Terada

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

87 Citations (Scopus)

Abstract

The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh₃)₄ without solvent at 130 °C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis.

Original language	English
Pages (from-to)	1055-1058
Number of pages	4
Journal	Organic letters
Volume	11
Issue number	5
DOIs	https://doi.org/10.1021/ol900113f
Publication status	Published - 2009 Mar 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes",

abstract = "The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh3)4 without solvent at 130 °C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis.",

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T1 - Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes

AU - Nakamura, Ltaru

AU - Nemoto, Tetsuya

AU - Shiraiwa, Naozumi

AU - Terada, Masahiro

PY - 2009/3/5

Y1 - 2009/3/5

N2 - The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh3)4 without solvent at 130 °C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis.

AB - The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh3)4 without solvent at 130 °C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis.

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Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes

Abstract

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