Iron-catalysed cross-coupling of organolithium compounds with organic halides

Zhenhua Jia; Qiang Liu; Xiao-Shui Peng; Henry N C Wong

doi:10.1038/ncomms10614

Iron-catalysed cross-coupling of organolithium compounds with organic halides

Nat Commun. 2016 Feb 5:7:10614. doi: 10.1038/ncomms10614.

Authors

Zhenhua Jia¹, Qiang Liu¹, Xiao-Shui Peng^{1

2}, Henry N C Wong^{1

2}

Affiliations

¹ Department of Chemistry, State Key Laboratory of Synthetic Chemistry and Centre of Novel Functional Molecules, Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
² Shenzhen Center of Novel Functional Molecules and Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute, Chinese University of Hong Kong, No.10, Second Yuexing Road, Shenzhen 518507, China.

Abstract

In past decades, catalytic cross-coupling reactions between organic halides and organometallic reagents to construct carbon-carbon bond have achieved a tremendous progress. However, organolithium reagents have rarely been used in cross-coupling reactions, due mainly to their high reactivity. Another limitation of this transformation using organolithium reagents is how to control reactivity with excellent selectivity. Although palladium catalysis has been applied in this field recently, the development of an approach to replace catalytic systems of noble metals with nonprecious metals is currently in high demand. Herein, we report an efficient synthetic protocol involving iron-catalysed cross-coupling reactions employing organolithium compounds as key coupling partners to unite aryl, alkyl and benzyl fragments and also disclose an efficient iron-catalysed release-capture ethylene coupling with isopropyllithium.

Publication types

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