Functionalization of sulfophthalocyanines in aqueous medium by palladium-catalyzed cross-coupling reactions

Modern Synthetic Tools Toward the Preparation of Sophisticated Phthalocyanine‐Based Photoactive Systems

“…In the context of water‐soluble phthalocyanines, van Lier initially reported a number of novel sulfonated derivatives, obtained through Sonogashira, Heck, and Suzuki couplings in aqueous media (Scheme ) 28. Specifically, cross‐coupling with a number of terminal alkynes in the presence of Pd(OAc) 2 and trisodium triphenylphosphine 3,3′,3′‐trisulfonate (TPPTS) as a ligand afforded alkyne‐substituted Pcs 15 a – f in good yields.…”

Synthetic approaches to asymmetric phthalocyanines and their analogues

“…In particular, as shown in the laboratories of Torres, van Lier, and many others, the mono-iodo A 3 B phthalocyanines 62 can easily be made to undergo a variety of coupling reactions (Scheme 23). 218,220,221,223,227,228,[236][237][238][239][240][241][242] This precursor can be used for the introduction of direct carboncarbon bonds as aryl, alkenyl, and alkynyl substituents. 217,219,220,226,234,235 In addition, the Buchwald reaction can be used for carbon-nitrogen bond formation.…”

Functionalisation of Phthalocyanines and Subphthalocyanines by Transition-Metal-Catalysed Reactions

“…Water-soluble trisulfonated monoiodoPcs 5 have been described by van Lier et al very recently (Scheme 5). 19 The synthesis implies to carry out the macrocyclisation reaction with phthalonitrile precursors having the sulfo groups protected as indole derivatives. After separation of the desired unsymmetrically substituted phthalocyanine derivative by column chromatography, deprotection with LiOMe yields the water-soluble monoiodophthalocyanine.…”

“…Thus, monoiodoPc 5 was reacted with sodium acrylate, Pd(OAc) 2 , Na 2 CO 3 and tris(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt (TXPT) as ligand, yielding 70-80% of compound 20 (Scheme 14). 19 Although the recent use of Ru-catalysed alkene crossmetathesis represented a significant breakthrough in alkene synthesis, there are only few examples in the literature in which the metathesis reaction has been applied to phtha-Scheme 15 Synthesis of a phthalocyanine polymer through olefin metathesis of phthalocyanine monomers 21 bearing terminal alkene groups locyanines. In particular, the olefin metathesis reaction has been applied to the synthesis of phthalocyanine polymers.…”