Gold- and indium-catalyzed synthesis of 3- and 6-sulfonylindoles from ortho-alkynyl-N-sulfonylanilines

Itaru Nakamura; Uichiro Yamagishi; Dschun Song; Sayaka Konta; Yoshinori Yamamoto

doi:10.1002/anie.200604038

Gold- and indium-catalyzed synthesis of 3- and 6-sulfonylindoles from ortho-alkynyl-N-sulfonylanilines

Itaru Nakamura, Uichiro Yamagishi, Dschun Song, Sayaka Konta, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

Tohoku University

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

208 Citations (Scopus)

Abstract

(Chemical Equation Presented) Consecutive formation of C-N and C-S bonds: The gold-catalyzed intramolecular aminosulfonylation of 2-alkynyl-N- sulfonylanilines 1 (R¹ = H) produces 3-sulfonylindoles 2 in good to high yields, whereas the indium-catalyzed aminosulfonylation of 2-alkynyl-6-methoxy-N-sulfonylanilines 1 (R¹ = MeO) affords 6-sulfonylindoles 3 as the major products (see scheme).

Original language	English
Pages (from-to)	2284-2287
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	13
DOIs	https://doi.org/10.1002/anie.200604038
Publication status	Published - 2007

Keywords

Cyclization
Fused-ring systems
Gold
Indium
Synthetic methods

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abstract = "(Chemical Equation Presented) Consecutive formation of C-N and C-S bonds: The gold-catalyzed intramolecular aminosulfonylation of 2-alkynyl-N- sulfonylanilines 1 (R1 = H) produces 3-sulfonylindoles 2 in good to high yields, whereas the indium-catalyzed aminosulfonylation of 2-alkynyl-6-methoxy-N-sulfonylanilines 1 (R1 = MeO) affords 6-sulfonylindoles 3 as the major products (see scheme).",

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T1 - Gold- and indium-catalyzed synthesis of 3- and 6-sulfonylindoles from ortho-alkynyl-N-sulfonylanilines

AU - Nakamura, Itaru

AU - Yamagishi, Uichiro

AU - Song, Dschun

AU - Konta, Sayaka

AU - Yamamoto, Yoshinori

PY - 2007

Y1 - 2007

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AB - (Chemical Equation Presented) Consecutive formation of C-N and C-S bonds: The gold-catalyzed intramolecular aminosulfonylation of 2-alkynyl-N- sulfonylanilines 1 (R1 = H) produces 3-sulfonylindoles 2 in good to high yields, whereas the indium-catalyzed aminosulfonylation of 2-alkynyl-6-methoxy-N-sulfonylanilines 1 (R1 = MeO) affords 6-sulfonylindoles 3 as the major products (see scheme).

KW - Cyclization

KW - Fused-ring systems

KW - Gold

KW - Indium

KW - Synthetic methods

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Gold- and indium-catalyzed synthesis of 3- and 6-sulfonylindoles from ortho-alkynyl-N-sulfonylanilines

Abstract

Keywords

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