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

Katie D. Mulholland; Sangbin Yoon; Christopher C. Rennie; Eleanor K. Sitch; Alasdair I. McKay; Katharina Edkins; Robert M. Edkins

doi:10.1039/D0CC03161E

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Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C_4h octaarylphthalocyanines†

Katie D. Mulholland,^a Sangbin Yoon,

^a Christopher C. Rennie,

^b Eleanor K. Sitch,^a Alasdair I. McKay,

^c Katharina Edkins

^d and Robert M. Edkins

*^b

Author affiliations

* Corresponding authors

^a Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK

^b WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow G1 1XL, UK
E-mail: robert.edkins@strath.ac.uk

^c School of Chemistry, Monash University, Clayton, VIC 3800, Australia

^d Division of Pharmacy and Optometry, University of Manchester, Stopford Building, Manchester M13 9PT, UK

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 C_4h 1,3,8,10,15,17,22,24-octaarylphthalocyanines.

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Article information

DOI: https://doi.org/10.1039/D0CC03161E
Article type: Communication
Submitted: 01 May 2020
Accepted: 18 Jun 2020
First published: 18 Jun 2020
This article is Open Access

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Chem. Commun., 2020,56, 8452-8455

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Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C_4h octaarylphthalocyanines

K. D. Mulholland, S. Yoon, C. C. Rennie, E. K. Sitch, A. I. McKay, K. Edkins and R. M. Edkins, Chem. Commun., 2020, 56, 8452 DOI: 10.1039/D0CC03161E

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