Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions

Deepak Kumar Barange; Veerababurao Kavala; B. Rama Raju; Chun Wei Kuo; Chi Tseng; Yu Chen Tu; Ching Fa Yao

doi:10.1016/j.tetlet.2009.06.107

Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions

Deepak Kumar Barange, Veerababurao Kavala, B. Rama Raju, Chun Wei Kuo, Chi Tseng, Yu Chen Tu, Ching Fa Yao

Department of Chemistry

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

24 Citations (Scopus)

Abstract

C-Alkylation of 2-hydroxy-1,4-naphthoquinone to various nitroolefins was achieved under catalyst-free employing 'on water' conditions. The mechanism for the formation can be explained on the basis of dual activation of nitroalkene and 2-hydroxy-1,4-naphthoquinones via hydrogen bonding. Simple reaction conditions, high yields of the products, and environmentally benign medium are attractive features of this method.

Original language	English
Pages (from-to)	5116-5119
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2009.06.107
Publication status	Published - 2009 Sep 9

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions. / Barange, Deepak Kumar; Kavala, Veerababurao; Raju, B. Rama; Kuo, Chun Wei; Tseng, Chi; Tu, Yu Chen; Yao, Ching Fa.

In: Tetrahedron Letters, Vol. 50, No. 36, 09.09.2009, p. 5116-5119.

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

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abstract = "C-Alkylation of 2-hydroxy-1,4-naphthoquinone to various nitroolefins was achieved under catalyst-free employing 'on water' conditions. The mechanism for the formation can be explained on the basis of dual activation of nitroalkene and 2-hydroxy-1,4-naphthoquinones via hydrogen bonding. Simple reaction conditions, high yields of the products, and environmentally benign medium are attractive features of this method.",

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note = "Funding Information: Financial support for this work by the National Science Council of the Republic of China is gratefully acknowledged. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

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AU - Barange, Deepak Kumar

AU - Kavala, Veerababurao

AU - Raju, B. Rama

AU - Kuo, Chun Wei

AU - Tseng, Chi

AU - Tu, Yu Chen

AU - Yao, Ching Fa

N1 - Funding Information: Financial support for this work by the National Science Council of the Republic of China is gratefully acknowledged. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

PY - 2009/9/9

Y1 - 2009/9/9

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AB - C-Alkylation of 2-hydroxy-1,4-naphthoquinone to various nitroolefins was achieved under catalyst-free employing 'on water' conditions. The mechanism for the formation can be explained on the basis of dual activation of nitroalkene and 2-hydroxy-1,4-naphthoquinones via hydrogen bonding. Simple reaction conditions, high yields of the products, and environmentally benign medium are attractive features of this method.

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Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions

Abstract

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