An efficient synthesis of bis-1,3-(3'-aryl-N-heterocycl-1'-yl)arenes as CCC-NHC pincer ligand precursors

Tyler O Howell; Aron J Huckaba; T Keith Hollis

doi:10.1021/ol5007407

An efficient synthesis of bis-1,3-(3'-aryl-N-heterocycl-1'-yl)arenes as CCC-NHC pincer ligand precursors

Org Lett. 2014 May 2;16(9):2570-2. doi: 10.1021/ol5007407. Epub 2014 Apr 15.

Authors

Tyler O Howell¹, Aron J Huckaba, T Keith Hollis

Affiliation

¹ Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.

PMID: 24735022
DOI: 10.1021/ol5007407

Abstract

A report that demonstrated an efficient methodology for the arylation of imidazoles has been extended to bis(N-heterocyclic) compounds. Using bis(aryl) iodonium salts provides high-yielding access to CCC-NHC ligand precursors in a single step. Examples of arylation using various iodonium salts are reported herein with an investigation into the factors governing their relative rate of reactivity. The metalation of one of these compounds using Zr(NMe2)4 and its subsequent treatment with [Pt(COD)Cl2] to yield a transmetalated product are reported.