Diverse secondary C(sp 3 )-H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines

We describe a coinage-metal-catalyzed site-selective oxidation of secondary C(sp )-H bonds for aliphatic amine substrates. Broad amine scope, good functional compatibility and late-stage diversification are demonstrated with this method. The steric demand of the β-substituents controlled diastereose...

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Veröffentlicht in:Chemical science (Cambridge) 2018-08, Vol.9 (30), p.6374-6378
Hauptverfasser: Tang, Yongzhen, Qin, Yuman, Meng, Dongmei, Li, Chaoqun, Wei, Junfa, Yang, Mingyu
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Sprache:eng
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Zusammenfassung:We describe a coinage-metal-catalyzed site-selective oxidation of secondary C(sp )-H bonds for aliphatic amine substrates. Broad amine scope, good functional compatibility and late-stage diversification are demonstrated with this method. The steric demand of the β-substituents controlled diastereoselectivities under this catalytic system. The site selectivity favors secondary C(sp )-H bonds over tertiary ones underscoring the unique synthetic potential of this method.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc01788c