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Synthesis 2023; 55(21): 3632-3643
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

Vikki N. Shinde‡
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
,
Bhawani Bhawani‡
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
,
Dhanajay S. Nipate
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
,
Sonam Sonam
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
,
Neha Meena
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
,
Krishnan Rangan
b   Department of Chemistry, Birla Institute of Technology and Science Pilani, Hyderabad Campus, Telangana 500078, India
,
Dalip Kumar
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
,
Anil Kumar  ∗
a   Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India
› Author AffiliationsFunding: 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.
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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 - manganese

Supporting Information



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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