Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes

Sachin Narute, Regev Parnes, F. Dean Toste, Doron Pappo

Research output: Contribution to journalArticlepeer-review

123 Scopus citations

Abstract

Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.

Original languageEnglish
Pages (from-to)16553-16560
Number of pages8
JournalJournal of the American Chemical Society
Volume138
Issue number50
DOIs
StatePublished - 21 Dec 2016

Fingerprint

Dive into the research topics of 'Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes'. Together they form a unique fingerprint.

Cite this