Iridium-catalysed 3,5-bis-borylation of phthalonitrile enables access to a family ofC(4h)octaarylphthalocyanines
Katie D Mulholland, Sangbin Yoon, Christopher C Rennie, Eleanor K Sitch, Alasdair McKay, Katharina Edkins, Robert M Edkins
CHEMICAL COMMUNICATIONS | ROYAL SOC CHEMISTRY | Published : 2020
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.
R. M. E. thanks the Royal Commission for the Exhibition of 1851 for a research fellowship, the John Fell Fund of the University of Oxford for a grant, the Analytical Chemistry Trust Fund for a summer studentship to S. B. Y., and AllyChem Co., Ltd for a gift of B2pin2. R. M. E. is grateful to Prof. Stephen Faulkner (University of Oxford) for providing laboratory space and generous support during his 1851 Fellowship.