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Synthesis 2023; 55(21): 3454-3469
DOI: 10.1055/a-2058-0695
DOI: 10.1055/a-2058-0695
special topic
C–H Bond Functionalization of Heterocycles
Transition-Metal-Catalyzed Directed C8–H Carbon–Carbon Bond Formation in Quinolines and 1,2,3,4-Tetrahydroquinolines
S.B. and S.M. thank Department of Science and Technology, Ministry of Science and Technology, India, for INSPIRE Senior Research Fellowship. T. Paul and M.V.N. are thankful to the Ministry of Education, India, for a Prime Minister’s Research Fellowship (PMRF). P.K. acknowledges the Ministry of Education, India, for a Senior Research Fellowship.
Abstract
C8-Substituted quinoline (QN) and 1,2,3,4-tetrahydroquinoline (THQ) scaffolds are featured in numerous bioactive compounds and natural products. Appreciable efforts have been made towards the development of elegant techniques to functionalize the C8–H bond of QNs and THQs. The transition-metal-catalyzed chelation-assisted C–H activation strategy has emerged as an effective synthetic tool among existing methods. This review focuses on recent advances in transition-metal-catalyzed directed carbon–carbon bond forming reactions for the C8–H functionalization of QNs and THQs (till February 2023). The discussion has been categorized based on the type of reaction.
1 Introduction
2 Acylation
3 Alkylation
4 Alkenylation
5 Alkynylation
6 Allylation
7 Annulation
8 Arylation
9 Conclusion and Outlook
Key words
quinoline - 1,2,3,4-tetrahydroquinoline - C–C bond formation - transition metal catalysis - directing groupPublication History
Received: 28 February 2023
Accepted after revision: 20 March 2023
Accepted Manuscript online:
20 March 2023
Article published online:
25 April 2023
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