Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride

Zhi Liang Shen; Kelvin Kau Kiat Goh; Hao Lun Cheong; Colin Hong An Wong; Yin Chang Lai; Yong Sheng Yang; Teck Peng Loh

doi:10.1021/ja106925f

Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride

Zhi Liang Shen, Kelvin Kau Kiat Goh, Hao Lun Cheong, Colin Hong An Wong, Yin Chang Lai, Yong Sheng Yang, Teck Peng Loh

Nanyang Technological University

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

98 Scopus citations

Abstract

The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl₃ to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl₂ was used in place of In/InCl₃. The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.

Original language	English
Pages (from-to)	15852-15855
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	132
Issue number	45
DOIs	https://doi.org/10.1021/ja106925f
State	Published - 17 Nov 2010
Externally published	Yes

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Shen, Z. L., Goh, K. K. K., Cheong, H. L., Wong, C. H. A., Lai, Y. C., Yang, Y. S., & Loh, T. P. (2010). Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride. Journal of the American Chemical Society, 132(45), 15852-15855. https://doi.org/10.1021/ja106925f

@article{e311871a15fc4f30a0b6854e7b17262b,

title = "Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride",

abstract = "The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl3 to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl2 was used in place of In/InCl3. The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.",

author = "Shen, {Zhi Liang} and Goh, {Kelvin Kau Kiat} and Cheong, {Hao Lun} and Wong, {Colin Hong An} and Lai, {Yin Chang} and Yang, {Yong Sheng} and Loh, {Teck Peng}",

year = "2010",

month = nov,

day = "17",

doi = "10.1021/ja106925f",

language = "英语",

volume = "132",

pages = "15852--15855",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "45",

}

Shen, ZL, Goh, KKK, Cheong, HL, Wong, CHA, Lai, YC, Yang, YS & Loh, TP 2010, 'Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride', Journal of the American Chemical Society, vol. 132, no. 45, pp. 15852-15855. https://doi.org/10.1021/ja106925f

Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride. / Shen, Zhi Liang; Goh, Kelvin Kau Kiat; Cheong, Hao Lun et al.
In: Journal of the American Chemical Society, Vol. 132, No. 45, 17.11.2010, p. 15852-15855.

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

TY - JOUR

T1 - Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride

AU - Shen, Zhi Liang

AU - Goh, Kelvin Kau Kiat

AU - Cheong, Hao Lun

AU - Wong, Colin Hong An

AU - Lai, Yin Chang

AU - Yang, Yong Sheng

AU - Loh, Teck Peng

PY - 2010/11/17

Y1 - 2010/11/17

N2 - The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl3 to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl2 was used in place of In/InCl3. The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.

AB - The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl3 to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl2 was used in place of In/InCl3. The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.

UR - http://www.scopus.com/inward/record.url?scp=78449251148&partnerID=8YFLogxK

U2 - 10.1021/ja106925f

DO - 10.1021/ja106925f

M3 - 文章

AN - SCOPUS:78449251148

SN - 0002-7863

VL - 132

SP - 15852

EP - 15855

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 45

ER -

Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride

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