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^*

^*Corresponding author for this work

Nanyang Technological University

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

99 Citations (Scopus)

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
Publication status	Published - Nov 17 2010
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja106925f

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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{e78e69b452bf4c3fb5031d33492e709b,

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 = "English",

volume = "132",

pages = "15852--15855",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

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}

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.

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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

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