Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols

Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc) /AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained wi...

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Veröffentlicht in:Organic & biomolecular chemistry 2017-01, Vol.15 (4), p.801-806
Hauptverfasser: Siva Reddy, A, Ranjith Reddy, K, Nageswar Rao, D, Jaladanki, Chaitanya K, Bharatam, Prasad V, Lam, Patrick Y S, Das, Parthasarathi
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Sprache:eng
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Zusammenfassung:Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc) /AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc) /Cs CO system and benzoic acid as an additive. These ligand-free conditions and "open-flask" chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02444k