One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

Xinbo Wang; Yupeng Pan; Kuo-Wei Huang; Zhiping Lai

doi:10.1021/acs.orglett.5b02881

One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

Xinbo Wang, Yupeng Pan, Kuo-Wei Huang, Zhiping Lai

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

17 Scopus citations

Abstract

A facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.

Original language	English (US)
Pages (from-to)	5630-5633
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.5b02881
State	Published - Nov 6 2015

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KAUST Repository Item: Exported on 2020-10-01

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10.1021/acs.orglett.5b02881

https://repository.kaust.edu.sa/bitstream/10754/583936/1/Xinbo%20Wang-org%20letts-2015.pdf

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title = "One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere",

abstract = "A facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.",

author = "Xinbo Wang and Yupeng Pan and Kuo-Wei Huang and Zhiping Lai",

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doi = "10.1021/acs.orglett.5b02881",

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T1 - One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

AU - Wang, Xinbo

AU - Pan, Yupeng

AU - Huang, Kuo-Wei

AU - Lai, Zhiping

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2015/11/6

Y1 - 2015/11/6

N2 - A facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.

AB - A facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.

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UR - http://pubs.acs.org/doi/10.1021/acs.orglett.5b02881

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DO - 10.1021/acs.orglett.5b02881

M3 - Article

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VL - 17

SP - 5630

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JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

Abstract

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CCDC 1438644: Experimental Crystal Structure Determination : 9-(1-(t-Butylperoxy)heptyl)-9H-carbazole

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One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

Abstract

Bibliographical note

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Datasets

CCDC 1438644: Experimental Crystal Structure Determination : 9-(1-(t-Butylperoxy)heptyl)-9H-carbazole

Cite this