Citation: Wu Zhen, Feng Xue-Xin, Wang Qing-Dong, Yun Jin-Jin, Rao Weidong, Yang Jin-Ming, Shen Zhi-Liang. Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α, β-unsaturated ketones[J]. Chinese Chemical Letters, ;2020, 31(5): 1297-1300. doi: 10.1016/j.cclet.2019.09.017 shu

Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α, β-unsaturated ketones

Wu Zhen ^a,b ,
Feng Xue-Xin ^a,b ,
Wang Qing-Dong ^b ,
Yun Jin-Jin ^a ,
Rao Weidong ^c ,
Yang Jin-Ming ^a,b,*, ,
Shen Zhi-Liang ^a,*,

a.
School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
b.
School of Pharmacy, Yancheng Teachers University, Yancheng 224007, China
c.
Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

yangjm@yctu.edu.cn

ias_zlshen@njtech.edu.cn

Received Date: 22 June 2019
Revised Date: 27 August 2019
Accepted Date: 9 September 2019
Available Online: 11 September 2019

An efficient method was developed for the conjugate addition of water to various α, β-unsaturated ketones by using bismuth(Ⅲ) chloride as a catalyst. The reactions proceeded smoothly in the presence of a catalytic amount of BiCl₃ (20 mol%) in aqueous media to furnish a variety of synthetically useful β-hydroxyl ketones in moderate to good yields. Apart from water molecule, various alcohols could also be employed as nucleophiles to react with α, β-unsaturated ketones, leading to β-alkoxyl ketones in modest to high yields. In addition, the mild reaction conditions also entailed the conjugate addition reactions to proceed with the tolerance to a range of functional groups.
- Bismuth trichloride,
- Water,
- β-Hydroxyl carbonyl compound,
- Michael addition,
- Functional group tolerance
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