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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Direct Nucleophilic Attack/Addition Cyclization and C-H Bond Activation Reactions to Synthesize
Dehe Wang1, Lingyu Zhao2, Yongjun Zhang1
1School of Chemistry and Chemical Engineering, Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. China.
Abstract:
The economic and practical strategies of direct nucleophilic attack/addition cyclization and C-H bond activation reactions to synthesize 3-benzyl-/3-benzyl-2-phenyl-benzo[4,5]imidazo[2,1-b]thiazoles via (Z)-(2,3-dibromoprop-1-en-1-yl)benzene/(3-bromoprop-1-yn-1-yl)benzene, 1H-benzo[d]imidazole-2-thiols and halobenzenes have been developed. With the optimized reaction conditions, the nucleophilic attack/addition cyclization reaction (Cs2CO3, MeCN, 90 °C, 24 h) and C-H bond activation reaction [Pd(OAc)2/PPh3, p-xylene, 135 °C, 24 h] could tolerate various electron-donating and electron-withdrawing groups and afford new benzo[4,5]imidazo[2,1-b]thiazoles in good to excellent yields (up to 93% yield).
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