Ruthenium-catalysed -selective C-H bond alkylation a deaminative strategy

The use of aliphatic amines as alkylating reagents in organic synthesis via C-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis of meta -alkylated arenes via dual C-H and C-N activation. Bench-stable and e...

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Published in:Chemical communications (Cambridge, England) England), 2021-04, Vol.57 (27), p.3411-3414
Main Authors: Zhu, Ze-Fan, Chen, Guang-Le, Liu, Feng
Format: Article
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Summary:The use of aliphatic amines as alkylating reagents in organic synthesis via C-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis of meta -alkylated arenes via dual C-H and C-N activation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amines and amino acid species were used as alkyl radical precursors. This catalytic reaction could accommodate a broad range of functional groups and provide access to various meta -alkylated products. The utilization of readily prepared Katritzky salts as radical precursors for remote meta -C Ar -H bond alkylation is described.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc00039j