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Synfacts 2020; 16(06): 0663
DOI: 10.1055/s-0040-1707804
DOI: 10.1055/s-0040-1707804
Metals in Synthesis
Manganese-Catalyzed Methylation of C(sp3)–H Bonds α to Heteroatoms
Further Information
Publication History
Publication Date:
15 May 2020 (online)
Key words
C–H functionalization - methylation - late-stage diversification - manganese catalysis - C–C bond formationSignificance
White and co-workers report a chemoselective C(sp3)–H methylation of heterocycles by using a three-step protocol. The method was applied to a broad substrate scope, including drug molecules, peptides, and natural products. The ability to introduce a ‘magic methyl’ group in certain pharmacologically relevant compounds has been shown to significantly improve their bioactivity.
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Comment
The authors combined a manganese-catalyzed methylene hydroxylation with subsequent iminium/oxonium formation and methylation to achieve the functionalization of various heterocyclic cores α to the heteroatom. The transformation proceeds at low catalyst loading with remarkable chemoselectivity and moderate to good overall yields.
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