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Synthesis 2023; 55(21): 3632-3643
DOI: 10.1055/a-2066-1131
DOI: 10.1055/a-2066-1131
special topic
C–H Bond Functionalization of Heterocycles
Manganese-Catalyzed ortho-Hydroalkylation of Aryl-Substituted N-Heteroaromatic Compounds with Maleimides
Funding: Science and Engineering Research Board (SERB New Delhi, CRG/2020/002220) and Department of Science and Technology, Ministry of Science and Technology, India (DST-FIST, SR/FST/CSI-270/2015). V.N.S. and D.S.N. thank the Council of Scientific and Industrial Research, India (CSIR New Delhi), N.M. thanks the University Grants Commission (UGC New Delhi) and Sonam and Bhawani thank the Birla Institute of Technology and Science Pilani (BITS Pilani) for fellowships.
Abstract
A regioselective manganese-catalyzed ortho-hydroalkylation of aryl-substituted N-heteroaromatic compounds with a range of maleimides is described. The developed C–H bond functionalization protocol allowed the introduction of the succinimide motif at the ortho-position of the aryl ring of N-heteroaromatic compounds, such as 2-arylimidazo[1,2-a]pyridines, 2-arylindazoles, 2-phenylpyridine, 2-phenylpyrimidine, 2-phenylimidazo[1,2-a]pyrimidine, 2-phenylimidazo[2,1-b]thiazole, 2-phenylbenzo[d]imidazo[2,1-b]thiazole, 1-phenylindazole and 1-phenylpyrazole, to produce 3-(2-(N-heteroaryl)aryl)pyrrolidine-2,5-diones in good yields. The protocol exhibited broad substrate scope, good functional group tolerance and excellent regioselectivity under mild and additive-free reaction conditions.
Key words
C–H functionalization - N-heteroaromatic compounds - hydroalkylation - maleimides - manganeseSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2066-1131.
- Supporting Information
- CIF File
Publication History
Received: 20 February 2023
Accepted after revision: 30 March 2023
Accepted Manuscript online:
03 April 2023
Article published online:
26 June 2023
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