Iodide-Ion-Catalyzed Carbon–Carbon Bond-Forming Cross-Dehydrogenative Coupling for the Synthesis of Indole Derivatives

Zhenhua Jia; Takashi Nagano; Xingshu Li; Albert S.C. Chan

doi:10.1002/ejoc.201201585

Iodide-Ion-Catalyzed Carbon–Carbon Bond-Forming Cross-Dehydrogenative Coupling for the Synthesis of Indole Derivatives

Zhenhua Jia, Takashi Nagano^*, Xingshu Li^*, Albert S.C. Chan

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

54 Citations (Scopus)

Abstract

The nBu₄NI-catalyzed intramolecular cross-dehydrogenative coupling (CDC) reaction has been applied to the synthesis of 1H-indole derivatives. Intramolecular oxidative coupling of N-arylenamines proceeded in the presence of a catalytic amount of nBu₄NI and tert-butyl hydroperoxide (TBHP) to afford the corresponding 1H-indole derivatives in good-to-excellent yields. A preliminary study of the synthesis of 3H-indole is also reported. This is a rare example of the nBu₄NI-catalyzed C-C bond-forming CDC reaction.

Original language	English
Pages (from-to)	858-861
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2013
Issue number	5
DOIs	https://doi.org/10.1002/ejoc.201201585
Publication status	Published - Feb 2013

User-Defined Keywords

Cross-coupling
Homogeneous catalysis
Iodine
Nitrogen heterocycles
Oxidation
Synthetic methods

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10.1002/ejoc.201201585

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title = "Iodide-Ion-Catalyzed Carbon–Carbon Bond-Forming Cross-Dehydrogenative Coupling for the Synthesis of Indole Derivatives",

abstract = "The nBu4NI-catalyzed intramolecular cross-dehydrogenative coupling (CDC) reaction has been applied to the synthesis of 1H-indole derivatives. Intramolecular oxidative coupling of N-arylenamines proceeded in the presence of a catalytic amount of nBu4NI and tert-butyl hydroperoxide (TBHP) to afford the corresponding 1H-indole derivatives in good-to-excellent yields. A preliminary study of the synthesis of 3H-indole is also reported. This is a rare example of the nBu4NI-catalyzed C-C bond-forming CDC reaction.",

keywords = "Cross-coupling, Homogeneous catalysis, Iodine, Nitrogen heterocycles, Oxidation, Synthetic methods",

author = "Zhenhua Jia and Takashi Nagano and Xingshu Li and Chan, {Albert S.C.}",

note = "Publisher copyright: {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2013",

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doi = "10.1002/ejoc.201201585",

language = "English",

volume = "2013",

pages = "858--861",

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T1 - Iodide-Ion-Catalyzed Carbon–Carbon Bond-Forming Cross-Dehydrogenative Coupling for the Synthesis of Indole Derivatives

AU - Jia, Zhenhua

AU - Nagano, Takashi

AU - Li, Xingshu

AU - Chan, Albert S.C.

PY - 2013/2

Y1 - 2013/2

N2 - The nBu4NI-catalyzed intramolecular cross-dehydrogenative coupling (CDC) reaction has been applied to the synthesis of 1H-indole derivatives. Intramolecular oxidative coupling of N-arylenamines proceeded in the presence of a catalytic amount of nBu4NI and tert-butyl hydroperoxide (TBHP) to afford the corresponding 1H-indole derivatives in good-to-excellent yields. A preliminary study of the synthesis of 3H-indole is also reported. This is a rare example of the nBu4NI-catalyzed C-C bond-forming CDC reaction.

AB - The nBu4NI-catalyzed intramolecular cross-dehydrogenative coupling (CDC) reaction has been applied to the synthesis of 1H-indole derivatives. Intramolecular oxidative coupling of N-arylenamines proceeded in the presence of a catalytic amount of nBu4NI and tert-butyl hydroperoxide (TBHP) to afford the corresponding 1H-indole derivatives in good-to-excellent yields. A preliminary study of the synthesis of 3H-indole is also reported. This is a rare example of the nBu4NI-catalyzed C-C bond-forming CDC reaction.

KW - Cross-coupling

KW - Homogeneous catalysis

KW - Iodine

KW - Nitrogen heterocycles

KW - Oxidation

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84873427160&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201201585

DO - 10.1002/ejoc.201201585

M3 - Journal article

AN - SCOPUS:84873427160

SN - 1434-193X

VL - 2013

SP - 858

EP - 861

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 5

ER -

Iodide-Ion-Catalyzed Carbon–Carbon Bond-Forming Cross-Dehydrogenative Coupling for the Synthesis of Indole Derivatives

Abstract

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