A Non-Cross-Coupling Approach to Arene-Bridged Macrocycles: Synthesis, Structure, and Direct, Regioselective Functionalization of a Cycloparaphenylene Fragment | Zendy

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

Open Access

A Non-Cross-Coupling Approach to Arene-Bridged Macrocycles: Synthesis, Structure, and Direct, Regioselective Functionalization of a Cycloparaphenylene Fragment

Author(s) -

Nirmal K. Mitra,

Rolande Meudom,

John D. Gorden,

Bradley L. Merner

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b01102

Subject(s) - regioselectivity , chemistry , surface modification , halogenation , stereochemistry , fragment (logic) , structural isomer , terphenyl , phenylene , combinatorial chemistry , organic chemistry , catalysis , polymer , computer science , programming language

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.

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