Cu(i)- and Au(i)-catalyzed regioselective oxidation of diynes: divergent synthesis of N-heterocycles

Catalyst-dependent oxidative cyclization of diynes with pyridine N-oxides is achieved using an amide directing group. Non-polarized and aminated alkyne could be selectively activated by copper and gold, thus leading to divergent synthesis of a range of pyrroles and dihydroindeno[1,2-c]pyrrol-3(2H)-o...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-09, Vol.8 (18), p.4960-4966
Main Authors: Wen-Bo, Shen, Ting-Ting, Zhang, Zhang, Meng, Jing-Jing, Wu, Xiao-Lei, Jiang, Guang-Xin Ru, Guang-Qin Gao, Xiu-Hong Zhu
Format: Article
Language:English
Subjects:
Alkynes
Catalysts
Copper
Crystallography
Divergence
Gold
N-Oxides
Organic chemistry
Oxidation
Pyrroles
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Summary:Catalyst-dependent oxidative cyclization of diynes with pyridine N-oxides is achieved using an amide directing group. Non-polarized and aminated alkyne could be selectively activated by copper and gold, thus leading to divergent synthesis of a range of pyrroles and dihydroindeno[1,2-c]pyrrol-3(2H)-ones. It should be noted that this difference might be attributed to the multicoordinated Cu center and the linearly aligned dicoordinated Au center.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo00912e