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

Mulholland, Katie D. and Yoon, Sangbin and Rennie, Christopher C. and Sitch, Eleanor K. and McKay, Alasdair I. and Edkins, Katharina and Edkins, Robert M. (2020) Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family of C4h octaarylphthalocyanines. Chemical Communications, 56 (60). pp. 8452-8455. ISSN 1359-7345 (https://doi.org/10.1039/D0CC03161E)

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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.

ORCID iDs

Mulholland, Katie D., Yoon, Sangbin, Rennie, Christopher C., Sitch, Eleanor K., McKay, Alasdair I., Edkins, Katharina ORCID logoORCID: https://orcid.org/0000-0002-6885-5457 and Edkins, Robert M. ORCID logoORCID: https://orcid.org/0000-0001-6117-5275;
CORE (COnnecting REpositories)