Citation: Xu Xinbin, Cheng Ruofei, Qiu Zaozao, Pan Chengling. Palladium-Catalyzed Cross-Coupling Reactions of Borylated o-Carborane: Synthesis of 3, 6-Diaryl-o-carboranes[J]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 3078-3085. doi: 10.6023/cjoc201805018 shu

Palladium-Catalyzed Cross-Coupling Reactions of Borylated o-Carborane: Synthesis of 3, 6-Diaryl-o-carboranes

Xu Xinbin ^a,b ,
Cheng Ruofei ^b ,
Qiu Zaozao ^b,, ,
Pan Chengling ^a,,

a.
Laboratory of Multiscale Materials and Molecular Catalysis, School of Materials Science and Engineering, Anhui University of Science and Technology, Huainan 232001
b.
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Qiu Zaozao, qiuzz@sioc.ac.cn Pan Chengling, clpan@aust.edu.cn
Received Date: 7 May 2018
Revised Date: 20 June 2018
Available Online: 5 November 2018
Fund Project: Project supported by the the National Natural Science Foundation of China (No. 21772223) and the CAS-Croucher Funding Schemethe the National Natural Science Foundation of China 21772223

Figures(3)

Palladium catalyzed cross-coupling of 3, 6-(Bpin)₂-o-carborane (Bpin=pinacolatoboryl) with aryl bromides has been achieved, leading to the formation of a series of B(3, 6)-diarylated-o-carborane derivatives in moderate yields. In this reaction, PdCl₂(cod)/tricyclohexylphosphine was used as catalyst to avoid the formation of palladium-catalyzed aryl-aryl exchange and direct B-H arylation by-products. A possible mechanism is proposed, involving a tandem sequence of oxidative addition, anion exchange, transmetalation, and reductive elimination.
- carborane,
- coupling reaction,
- palladium,
- carboranyl boronate,
- aryl bromide
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