Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines

Nianyuan Tan; Shuangfeng Yin; Yuefang Li; Renhua Qiu; Zhengong Meng; Xingxing Song; Shenglian Luo; Chak Tong AU; Wai Yeung WONG

doi:10.1016/j.jorganchem.2010.12.035

Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines

Nianyuan Tan, Shuangfeng Yin^*, Yuefang Li, Renhua Qiu, Zhengong Meng, Xingxing Song, Shenglian Luo, Chak Tong AU, Wai Yeung WONG

^*Corresponding author for this work

Department of Chemistry

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

43 Citations (Scopus)

Abstract

An air-stable organobismuth triflate complex with a novel 5,6,7,12-tetrahydrodibenzo[c,f]-[1,5]oxabismocine framework was synthesized and characterized by spectroscopic and single-crystal X-ray diffraction techniques. The organobismuth framework is cationic, and the complex shows relatively strong Lewis acidity (0.8 < H_o ≤ 3.3). It was found to exhibit high catalytic activity towards the ring-opening reaction of epoxides in aqueous media with aromatic amines at room temperature. This catalyst shows good stability, recyclability and reusability. The catalytic system affords a simple and efficient method for the synthesis of β-amino alcohols.

Original language	English
Pages (from-to)	1579-1583
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	696
Issue number	8
DOIs	https://doi.org/10.1016/j.jorganchem.2010.12.035
Publication status	Published - 15 Apr 2011

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

User-Defined Keywords

β-Amino alcohol
5,6,7,12-tetrahydrodibenzo[c,f][1,5]oxabismocine framework
Cationic organobismuth complex
Epoxide
Ring-opening reaction

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10.1016/j.jorganchem.2010.12.035

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Tan, N., Yin, S., Li, Y., Qiu, R., Meng, Z., Song, X., Luo, S., AU, C. T., & WONG, W. Y. (2011). Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines. Journal of Organometallic Chemistry, 696(8), 1579-1583. https://doi.org/10.1016/j.jorganchem.2010.12.035

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title = "Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines",

abstract = "An air-stable organobismuth triflate complex with a novel 5,6,7,12-tetrahydrodibenzo[c,f]-[1,5]oxabismocine framework was synthesized and characterized by spectroscopic and single-crystal X-ray diffraction techniques. The organobismuth framework is cationic, and the complex shows relatively strong Lewis acidity (0.8 < Ho ≤ 3.3). It was found to exhibit high catalytic activity towards the ring-opening reaction of epoxides in aqueous media with aromatic amines at room temperature. This catalyst shows good stability, recyclability and reusability. The catalytic system affords a simple and efficient method for the synthesis of β-amino alcohols.",

keywords = "β-Amino alcohol, 5,6,7,12-tetrahydrodibenzo[c,f][1,5]oxabismocine framework, Cationic organobismuth complex, Epoxide, Ring-opening reaction",

author = "Nianyuan Tan and Shuangfeng Yin and Yuefang Li and Renhua Qiu and Zhengong Meng and Xingxing Song and Shenglian Luo and AU, {Chak Tong} and WONG, {Wai Yeung}",

note = "Funding Information: This work was financially supported by the Project supported by Hunan Provincial Natural Science Foundation of China ( 10JJ1003 ), the NSFC (Grant Nos. 20973056 , J0830415 ), the National 863 Program of China ( 2009AA05Z319 ), and the Outstanding Young Research Award of NSFC (Grant No E50725825 ). C.T. Au thanks the HNU for an adjunct professorship. C.T. Au and W.-Y. Wong thank the Hong Kong Baptist University for a Faculty Research Grant ( FRG/08-09/II-09 ). ",

year = "2011",

month = apr,

day = "15",

doi = "10.1016/j.jorganchem.2010.12.035",

language = "English",

volume = "696",

pages = "1579--1583",

journal = "Journal of Organometallic Chemistry",

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Tan, N, Yin, S, Li, Y, Qiu, R, Meng, Z, Song, X, Luo, S, AU, CT & WONG, WY 2011, 'Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines', Journal of Organometallic Chemistry, vol. 696, no. 8, pp. 1579-1583. https://doi.org/10.1016/j.jorganchem.2010.12.035

Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines. / Tan, Nianyuan; Yin, Shuangfeng; Li, Yuefang et al.
In: Journal of Organometallic Chemistry, Vol. 696, No. 8, 15.04.2011, p. 1579-1583.

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

TY - JOUR

T1 - Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines

AU - Tan, Nianyuan

AU - Yin, Shuangfeng

AU - Li, Yuefang

AU - Qiu, Renhua

AU - Meng, Zhengong

AU - Song, Xingxing

AU - Luo, Shenglian

AU - AU, Chak Tong

AU - WONG, Wai Yeung

N1 - Funding Information: This work was financially supported by the Project supported by Hunan Provincial Natural Science Foundation of China ( 10JJ1003 ), the NSFC (Grant Nos. 20973056 , J0830415 ), the National 863 Program of China ( 2009AA05Z319 ), and the Outstanding Young Research Award of NSFC (Grant No E50725825 ). C.T. Au thanks the HNU for an adjunct professorship. C.T. Au and W.-Y. Wong thank the Hong Kong Baptist University for a Faculty Research Grant ( FRG/08-09/II-09 ).

PY - 2011/4/15

Y1 - 2011/4/15

N2 - An air-stable organobismuth triflate complex with a novel 5,6,7,12-tetrahydrodibenzo[c,f]-[1,5]oxabismocine framework was synthesized and characterized by spectroscopic and single-crystal X-ray diffraction techniques. The organobismuth framework is cationic, and the complex shows relatively strong Lewis acidity (0.8 < Ho ≤ 3.3). It was found to exhibit high catalytic activity towards the ring-opening reaction of epoxides in aqueous media with aromatic amines at room temperature. This catalyst shows good stability, recyclability and reusability. The catalytic system affords a simple and efficient method for the synthesis of β-amino alcohols.

AB - An air-stable organobismuth triflate complex with a novel 5,6,7,12-tetrahydrodibenzo[c,f]-[1,5]oxabismocine framework was synthesized and characterized by spectroscopic and single-crystal X-ray diffraction techniques. The organobismuth framework is cationic, and the complex shows relatively strong Lewis acidity (0.8 < Ho ≤ 3.3). It was found to exhibit high catalytic activity towards the ring-opening reaction of epoxides in aqueous media with aromatic amines at room temperature. This catalyst shows good stability, recyclability and reusability. The catalytic system affords a simple and efficient method for the synthesis of β-amino alcohols.

KW - β-Amino alcohol

KW - 5,6,7,12-tetrahydrodibenzo[c,f][1,5]oxabismocine framework

KW - Cationic organobismuth complex

KW - Epoxide

KW - Ring-opening reaction

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U2 - 10.1016/j.jorganchem.2010.12.035

DO - 10.1016/j.jorganchem.2010.12.035

M3 - Journal article

AN - SCOPUS:79953652363

SN - 0022-328X

VL - 696

SP - 1579

EP - 1583

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 8

ER -

Synthesis and structure of an air-stable organobismuth triflate complex and its use as a high-efficiency catalyst for the ring opening of epoxides in aqueous media with aromatic amines

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