Poly Heck coupling

The coupling reaction of aryl-alkenyl halides with alkenes in the presence of a palladium catalyst and a base is known as the Heck coupling (Scheme 9.4).6 Since the early 1980s, this type of coupling reaction has been used for die syndiesis of poly(arylenevinylene) and related polymers by polymerization of AB- or AA/BB-type of monomers (Scheme 9.5).7... 

Scheme 6.6 Heck coupling of iodobenzene and styrene as a model reaction for micellar catalysis using triphenylphosphine-functionalized poly(2-oxazoline)s as macroligands...

The dibromo- (and diiodo-) stilbenes ate potentially useful monomers tor the synthesis of poly(p-phenylenevinylenes) via poly-Heck or poly-Suzuki coupling reactions. ... 

In a similar approach, p-phenylene vinylene oligomers containing 3- to 6-mers have been grown on DOPO-Br capped NCs by homocoupling of l-bromo-2,5-di-n-octyl-4-vinylbenzene.133 Finally, using a one-step procedure, vinyl-terminated poly(hexylthiophene) has been grafted onto DOPO-Br coated NCs via Heck coupling.134... 

The application of Heck coupling polycondensation is not limited to the synthesis of poly(arylene vinylene)s via the alkenylation of haloarenes in simple monomer systems but includes a variety of self- and cross-coupling reactions involving reactants with various functionalities. For instance, the polycondensation of diiodoarene with bis(acrylamido)arene by the Pd(OOCCH3)2—P (o-C6H4—CH3)3 catalyst yields respective aromatic polycinnamamide [106] ... 

Aromatic 1,3,4-oxadiazoles are known to be efficient electron transport materials. When incorporated by Heck coupling into the poly(phenylene) chain in polymers such as 38, the electron carrier mobilities are indeed increased, while the hole mobilities are unchanged [75]. Light-emitting diodes prepared from this polymer show increasingly metal-dominated emission as the %Ru content is increased. 

In catalytic Pd(0) reactions, this phosphonium salt was treated with a Pd(ll) source, base, and substrates to form an active catalyst for Sonogashira, Suzuki, and Heck coupling chemistry (Eq. 42, Eq. 43, Eq. 44). The reactions used 0.5 mol% of the Pd catalyst, >99.9% of which was recovered based on Pd analysis of the filtrate of a nanofiltration using UV-visible and total reflection X-ray fluorescence analysis. The spectroscopic analyses reportedly could detect as little as 0.05% of the 0.01 mmol of starting Pd catalyst in the leachate. The membrane used in this chemistry was a solvent-resistant nanofiltration membrane consisting of a porous poly(acrylonitrile) layer and a dense surface layer of poly(dimethylsiloxane). This membrane worked through nine cycles in the... 

A Heck coupling reaction of l,4-diiodo-2,5-dialkoxybenzene with the bis(vinylphenyl)-substituted porphyrin 44 led to soluble and processable poly-... 

Bao, Z., et al. 1993. Conjugated liquid-crystalline polymers—Soluble and fusible poly(phenylene-vinylene) by the Heck coupling reaction. Macromolecules 26 5281. 

Over the past decade, literally dozens of new AB2-type monomers have been reported leading to an enormously diverse array of hyperbranched structures. Some general types include poly(phenylenes) obtained by Suzuki-coupling [54, 55], poly(phenylacetylenes prepared by Heck-reaction [58], polycarbosilanes, polycarbosiloxanes [59], and polysiloxysilanes by hydrosilylation [60], poly(ether ketones) by nucleophilic aromatic substitution [61] and polyesters [62] or polyethers by polycondensations [63] or by ring opening [64]. 

Bergbreiter reported that poly(N-isopropylacrylamide)-bound phosphine ligands (PNIPAM-resins) coordinated with the Pd(0) moieties afford efficient catalysts (46) for the Heck, Suzuki and sp-sp cross-coupling reactions (Scheme 4.30) [122]. 

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