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^*

^*Corresponding author for this work

Department of Chemistry

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

26 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 Sept 9

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.06.107

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

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.",

author = "Barange, {Deepak Kumar} and Veerababurao Kavala and Raju, {B. Rama} and Kuo, {Chun Wei} and Chi Tseng and Tu, {Yu Chen} and Yao, {Ching Fa}",

note = "Funding Information: Financial support for this work by the National Science Council of the Republic of China is gratefully acknowledged. ",

year = "2009",

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doi = "10.1016/j.tetlet.2009.06.107",

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T1 - Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions

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.

PY - 2009/9/9

Y1 - 2009/9/9

N2 - 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.

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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DO - 10.1016/j.tetlet.2009.06.107

M3 - Article

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SN - 0040-4039

VL - 50

SP - 5116

EP - 5119

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

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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CCDC 720909: Experimental Crystal Structure Determination

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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

ASJC Scopus subject areas

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Datasets

CCDC 720909: Experimental Crystal Structure Determination

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