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Issue 7, 2012
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Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes

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Abstract

The first size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes (CPP) has been achieved by strategically utilizing cis-1,4-diphenylcyclohexane-1,4-diyl as the key terphenyl-convertible L-shaped unit. To access the designed triangular or rectangular macrocyclic precursors, we utilized palladium-catalysed C–B/C–Br cross-coupling (Suzuki–Miyaura coupling) and/or nickel-mediated C–Br/C–Br coupling. We also established step-economical routes to [14] and [16]CPP using nickel-mediated C–Br/C–Br coupling. The final aromatization steps toward CPPs were accomplished with NaHSO4. Thus, combined with our previous size-selective synthesis of [12] and [14]–[16]CPP, we completed our size-selective synthesis of [9]–[16]CPP. The successful size-selective syntheses of [n]CPPs speak well for the flexibility and reliability of our strategy using a cyclohexane ring.

Graphical abstract: Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes

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Supplementary files

Article information


Submitted
19 Mar 2012
Accepted
11 Apr 2012
First published
11 Apr 2012

Chem. Sci., 2012,3, 2340-2345
Article type
Edge Article

Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes

Y. Ishii, Y. Nakanishi, H. Omachi, S. Matsuura, K. Matsui, H. Shinohara, Y. Segawa and K. Itami, Chem. Sci., 2012, 3, 2340
DOI: 10.1039/C2SC20343J

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