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

Sachin Narute; Regev Parnes; F Dean Toste; Doron Pappo

doi:10.1021/jacs.6b11198

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

J Am Chem Soc. 2016 Dec 21;138(50):16553-16560. doi: 10.1021/jacs.6b11198. Epub 2016 Dec 13.

Authors

Sachin Narute¹, Regev Parnes¹, F Dean Toste², Doron Pappo¹

Affiliations

¹ Department of Chemistry, Ben-Gurion University of the Negev , Beer-Sheva 84105, Israel.
² Department of Chemistry, University of California , Berkeley, California 94720, United States.

PMID: 27959518
DOI: 10.1021/jacs.6b11198

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.

Publication types

Research Support, Non-U.S. Gov't