Citation: Wu Yan, Luo Fan, Pan Shimin, Li Yuhan, He Shuhua. Nickel-Catalyzed Coupling of 1, 2-Diarylthio-1, 2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2946-2951. doi: 10.6023/cjoc201904050 shu

Nickel-Catalyzed Coupling of 1, 2-Diarylthio-1, 2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes

Chongqing Key Laboratory of Inorganic Special Functional Materials, College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling 408000

Corresponding author: He Shuhua, thshuhua@163.com
Received Date: 20 April 2019
Revised Date: 14 May 2019
Available Online: 12 October 2019
Fund Project: the Basic and Frontier Research Project of Chongqing City Cstc2018jcyjAX0721the Youth Talent Growth Plan Project of Yangtze Normal University 2018QNRC11Project supported by the Basic and Frontier Research Project of Chongqing City (No.Cstc2018jcyjAX0721) and the Youth Talent Growth Plan Project of Yangtze Normal University (No.2018QNRC11)

Figures(1)

A convenient protocol for the synthesis of multi-substituted alkenes from (Z)-1, 2-diarylthio-1, 2-diarylalkenes with Grignard reagents was developed via the highly selective coupling of (Z)-1, 2-diarylthio-1, 2-diarylalkenes catalyzed by 5.0 mol% NiCl₂(dppe). The leaving organosulfur group could be converted to diaryldisulfide after hydrolysis and oxidation, which realized the recycling of sulfur resources, meeting the requirements of green chemistry. This process tolerated to different (Z)-1, 2-diarylthio-1, 2-diarylalkenes and Grignard reagents to deliver products in good to excellent yields, providing an efficient route to multi-substituted alkenes.
- nickel-catalyzed coupling,
- multi-substituted alkenes,
- (Z)-1, 2-diarylthio-1, 2-diarylalkenes,
- Grignard reagents
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