Citation: Hui Zhao, Rakesh Kumar Gupta, Wei Zhang, Jiong Jia, Qun Yu, Zhiyong Gao, Guilin Zhuang, Dacheng Li, Xingpo Wang, Chen Ho Tung, Di Sun. Facile one-pot synthesis of a novel all-carbon stair containing dimerized pentalene core from alkyne[J]. Chinese Chemical Letters, ;2022, 33(4): 2047-2051. doi: 10.1016/j.cclet.2021.10.036 shu

Facile one-pot synthesis of a novel all-carbon stair containing dimerized pentalene core from alkyne

Hui Zhao ^{a, 1} ,
Rakesh Kumar Gupta ^{a, 1} ,
Wei Zhang ^b ,
Jiong Jia ^a ,
Qun Yu ^a ,
Zhiyong Gao ^c ,
Guilin Zhuang ^{b, *,} ,
Dacheng Li ^d ,
Xingpo Wang ^{a, *,} ,
Chen Ho Tung ^a ,
Di Sun ^{a, *,}

a.
Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, State Key Laboratory of Crystal Materials, Shandong University, Ji'nan 250100, China
b.
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032, China
c.
School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang 453007, China
d.
Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, and School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000, China

glzhuang@zjut.edu.cn

xpw6@sdu.edu.cn

dsun@sdu.edu.cn

Received Date: 13 August 2021
Revised Date: 13 October 2021
Accepted Date: 15 October 2021
Available Online: 22 October 2021

Figures(7)

The construction of all-carbon molecule frameworks remains challenging. Herein, we report a facile and efficient one-pot synthesis of a novel all-carbon stair containing dimerized pentalene core using inexpensive cyclopropyl alkyne catalyzed by in situ generated Cu(I) from the comproportionation reaction of Cu(II) salt and Cu powder under mild reaction conditions. The reaction proceeds via sequential acetylenic coupling, followed by cyclization and [2 + 2] cycloaddition to directly produce pentalene dimer, which is difficult to access by other established methods. Different mechanistic paths were studied for the pentalene formation using density functional theory, suggesting that the reaction also proceeds through acetylenic coupling followed by cyclization and [2 + 2] cycloaddition. Based on the activation energy barriers, Path 1 has the rate-determining step of 38.63 kcal/mol, which is the most thermodynamically preferred one among the four paths.
- One-pot synthesis,
- Penatlene dimerization,
- Comproportionation reaction,
- Crystal structure,
- Theoretical calculations
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