A non-cross-coupling approach to arene-bridged macrocycles: synthesis, structure, and direct, regioselective functionalization of a cycloparaphenylene fragment

Nirmal K Mitra; Rolande Meudom; John D Gorden; Bradley L Merner

doi:10.1021/acs.orglett.5b01102

A non-cross-coupling approach to arene-bridged macrocycles: synthesis, structure, and direct, regioselective functionalization of a cycloparaphenylene fragment

Org Lett. 2015 Jun 5;17(11):2700-3. doi: 10.1021/acs.orglett.5b01102. Epub 2015 May 8.

Authors

Nirmal K Mitra¹, Rolande Meudom¹, John D Gorden¹, Bradley L Merner¹

Affiliation

¹ Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849, United States.

PMID: 25952474
DOI: 10.1021/acs.orglett.5b01102

Abstract

A new synthetic strategy that employs a relatively unstrained, 1,4-diketo-bridged macrocycle as a precursor to a strained, 1,4-arene-bridged (bent para-phenylene) macrocycle has been developed. The distorted p-terphenyl nucleus (CPP fragment) of the macrocycle has been characterized by X-ray crystallography, and a direct, regioselective bromination protocol of the macrocyclic system is reported.