Heterocoupling of 2-naphthols enabled by a copper-N-heterocyclic carbene complex.
The reactivity of a Cu catalyst for oxidative coupling is modulated by a small molecule additive, diethyl malonate, that slows over-oxidation of 2-naphthols. Efficient heterocoupling between electron-rich and electron-poor 2-naphthols/2-naphthylamines affords C(1)-symmetric BINOLs with yields ranging from 35-98%.
Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec, Canada H3C 3J7.
Michael
M
Holtz-Mulholland
Mylène
M
de Léséleuc
Shawn K
SK
Collins
D015081:2-Naphthylamine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
C493913:1-(2-aminonaphth-1-yl)-2-naphthol; C406944:BINOL, naphthol; D006571:Heterocyclic Compounds; D009284:Naphthols; D009942:Organometallic Compounds; C030011:carbene; D003300:Copper; D015081:2-Naphthylamine; D008697:Methane; C028405:2-naphthol