Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate

Renhua Qiu; Yimiao Qiu; Shuangfeng Yin; Xinhua Xu; Shenglian Luo; Chak Tong Au; Wai Yeung Wong; Shigeru Shimada

doi:10.1002/adsc.200900679

Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate

Renhua Qiu, Yimiao Qiu, Shuangfeng Yin^*, Xinhua Xu, Shenglian Luo, Chak Tong Au, Wai Yeung Wong, Shigeru Shimada

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

51 Citations (Scopus)

Abstract

An air-stable cationic organobismuth perfluorooctanesulfonate possessing both acidic and basic characters was synthesized, and showed high catalytic activity, diastereoselectivity, stability, and reusability in the one-pot synthesis of (E)-α,β-unsaturated ketones through highly selective crossed condensation of ketones and aldehydes in water.

Original language	English
Pages (from-to)	153-162
Number of pages	10
Journal	Advanced Synthesis & Catalysis
Volume	352
Issue number	1
DOIs	https://doi.org/10.1002/adsc.200900679
Publication status	Published - 4 Jan 2010

User-Defined Keywords

(e)-α,β-unsaturated ketones
Crossed condensation
Diastereoselectivity
Organobismuth compounds
Perfluorooctanesulfonates

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10.1002/adsc.200900679

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Qiu, R., Qiu, Y., Yin, S., Xu, X., Luo, S., Au, C. T., Wong, W. Y., & Shimada, S. (2010). Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate. Advanced Synthesis & Catalysis, 352(1), 153-162. https://doi.org/10.1002/adsc.200900679

@article{e48a687aa00a42d7a88a402de0c03019,

title = "Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate",

abstract = "An air-stable cationic organobismuth perfluorooctanesulfonate possessing both acidic and basic characters was synthesized, and showed high catalytic activity, diastereoselectivity, stability, and reusability in the one-pot synthesis of (E)-α,β-unsaturated ketones through highly selective crossed condensation of ketones and aldehydes in water.",

keywords = "(e)-α,β-unsaturated ketones, Crossed condensation, Diastereoselectivity, Organobismuth compounds, Perfluorooctanesulfonates",

author = "Renhua Qiu and Yimiao Qiu and Shuangfeng Yin and Xinhua Xu and Shenglian Luo and Au, {Chak Tong} and Wong, {Wai Yeung} and Shigeru Shimada",

year = "2010",

month = jan,

day = "4",

doi = "10.1002/adsc.200900679",

language = "English",

volume = "352",

pages = "153--162",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

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Qiu, R, Qiu, Y, Yin, S, Xu, X, Luo, S, Au, CT, Wong, WY & Shimada, S 2010, 'Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate', Advanced Synthesis & Catalysis, vol. 352, no. 1, pp. 153-162. https://doi.org/10.1002/adsc.200900679

Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate. / Qiu, Renhua; Qiu, Yimiao; Yin, Shuangfeng et al.
In: Advanced Synthesis & Catalysis, Vol. 352, No. 1, 04.01.2010, p. 153-162.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate

AU - Qiu, Renhua

AU - Qiu, Yimiao

AU - Yin, Shuangfeng

AU - Xu, Xinhua

AU - Luo, Shenglian

AU - Au, Chak Tong

AU - Wong, Wai Yeung

AU - Shimada, Shigeru

PY - 2010/1/4

Y1 - 2010/1/4

N2 - An air-stable cationic organobismuth perfluorooctanesulfonate possessing both acidic and basic characters was synthesized, and showed high catalytic activity, diastereoselectivity, stability, and reusability in the one-pot synthesis of (E)-α,β-unsaturated ketones through highly selective crossed condensation of ketones and aldehydes in water.

AB - An air-stable cationic organobismuth perfluorooctanesulfonate possessing both acidic and basic characters was synthesized, and showed high catalytic activity, diastereoselectivity, stability, and reusability in the one-pot synthesis of (E)-α,β-unsaturated ketones through highly selective crossed condensation of ketones and aldehydes in water.

KW - (e)-α,β-unsaturated ketones

KW - Crossed condensation

KW - Diastereoselectivity

KW - Organobismuth compounds

KW - Perfluorooctanesulfonates

UR - http://www.scopus.com/inward/record.url?scp=75749096015&partnerID=8YFLogxK

U2 - 10.1002/adsc.200900679

DO - 10.1002/adsc.200900679

M3 - Journal article

AN - SCOPUS:75749096015

SN - 1615-4150

VL - 352

SP - 153

EP - 162

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 1

ER -

Highly efficient and selective synthesis of (E)-α,β-unsaturated ketones by crossed condensation of ketones and aldehydes catalyzed by an air-stable cationic organobismuth perfluorooctanesulfonate

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