Citation: Zhenwei Shi, Wenxiu Mao, Zhenning Yang, Shuzhe Sun, Chen-Ho Tung, Zhenghu Xu. Au-catalyzed neighboring hydroxymethyl group directed cycloaddition of alkyne with diazadienes: Synthesis of polysubstituted pyrroles[J]. Chinese Chemical Letters, ;2023, 34(1): 107488. doi: 10.1016/j.cclet.2022.05.002 shu

Au-catalyzed neighboring hydroxymethyl group directed cycloaddition of alkyne with diazadienes: Synthesis of polysubstituted pyrroles

Zhenwei Shi ^a ,
Wenxiu Mao ^a ,
Zhenning Yang ^a ,
Shuzhe Sun ^a ,
Chen-Ho Tung ^a ,
Zhenghu Xu ^{a, b, *,}

a.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
b.
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, Hangzhou 310024, China

xuzh@sdu.edu.cn

Received Date: 29 January 2022
Revised Date: 27 April 2022
Accepted Date: 2 May 2022
Available Online: 8 May 2022

Figures(7)

Polysubstituted pyrroles are very important scaffolds in many bioactive natural products and synthetic pharmaceuticals. Here, a new gold-catalyzed cycloaddition of alkynes with azadienes to access tetrasubstituted pyrroles is demonstrated. The neighboring hydroxylmethyl group serves a very important directing group through an addition/cycloaddition/elimination cascade. Diverse polysubstituted pyrroles were synthesized in good yields under mild conditions in one step, and tricyclic pyrrole containing heterocycles were easily obtained through derivatization.
- Pyrrole,
- Au,
- Neighboring group,
- Cascade reaction,
- Synthetic method
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