Systematic Synthesis of Macrocycles Bearing up to Six 2,2'-Bipyridine Moieties through Self-Assembled Double Helix Structure.

J Org Chem

Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1, Komaba, Meguro-ku, Tokyo 153-8902, Japan.

Published: October 2022

A new synthetic strategy for macrocycles bearing multiple coordination moieties was developed. A self-assembled double helix structure, composed of two linear strands bearing 2,2'-bipyridine units and Cu(I) ions, provided access to macrocycles bearing a defined number of 2,2'-bipyridine moieties and a defined ring size, via an olefin-metathesis reaction between two linear strands in the helix. The double helix structure improved the selectivity of the macrocycle synthesis by bringing the reaction points in close proximity even in the case of large macrocycles.

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http://dx.doi.org/10.1021/acs.joc.2c01194DOI Listing

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