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Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

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Abstract

Ir-catalysed borylation of phthalonitrile produces both 4-(Bpin)phthalonitrile (1) and 3,5-bis(Bpin)phthalonitrile (2), which are potential divergent intermediates for the synthesis of functionalized phthalocyanines. To exemplify the utility of 2, we have prepared a series of 3,5-bis-arylphthalonitriles that in turn undergo sterically controlled regioselective cyclotetramization to give previously unknown C4h 1,3,8,10,15,17,22,24-octaarylphthalocyanines.

Graphical abstract: Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

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Article information


Submitted
01 May 2020
Accepted
18 Jun 2020
First published
18 Jun 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines

K. D. Mulholland, S. Yoon, C. C. Rennie, E. K. Sitch, A. I. McKay, K. Edkins and R. M. Edkins, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03161E

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