Hagihara cross-coupling

Fig. 7 Node-strut topology for series of CMPs networks produced by Sonagashira-Hagihara cross-coupling chemistry [19]. The benzene nodes are shown in red. The total number of ethyne plus benzene links per strut increases in increments of one from two (CMP-0) to six (CMP-5) in this series of samples. It should be stressed that these are simple representations of the repeat unit structures for the networks. The actual three-dimensional materials have more complex structures and include both terminal alkyne and halogen end groups (see also molecular simulations, Fig. 9)...

Scheme 1.8 (a) General conditions for the Songashira-Hagihara cross-coupling reaction, (b) The proposed mechanism for the Sonogashira-Hagihara cross-coupling arylation procedure [12, 24]. 

Sonogashira-Hagihara Cross-Coupling with Arenediazonium Salts - Synthesis of 1-(4-Methoxyphenyl)-2-phenylacetylene... 

Cooper prepared similar microporous poly(aryleneethynylene) (PAE) networks via Sonogashira-Hagihara cross-coupling reaction using 1,3,5-triethynyl benzene and 4,4"-diiodo-5 -(4-iodophenyl)-l,r 3, l"-terphenyl as trigonal and 1,4-diethynyl benzene and 1,4-diodo benzene as well as the corresponding biphenyl derivatives as linear... 

Palladium-catalyzed cross-coupling is a powerful tool for the synthesis of various 7c-conjugated molecules and polymers through sp and sp carbon-carbon bond formation [17-20]. Scheme 3 shows the synthetic routes for poly (p-arylene-ethynylene)-type (PAE-type) jc-stacked polymers by Sonogashira-Hagihara cross-coupling [21, 22]. Polymer 13 was obtained from the monomers pseudo-para-dibromo[2.2]... 

Using Pd-mediated cross-coupling reactions, such as Suzuki, Heck, and Sonoga-shira- Hagihara reaction, researchers efficiently constructed a library of 151 coumarin derivatives from eight 3-bromocoumarins cross-coupled with ten aryl/heteroaryl boronic acids, ten alkenes, and ten alkynes (Fig. 4). 

Cross-coupling of terminal acetylenes used as nucleophiles with aryl or alkenyl halides (referred to as the Sonogashira-Hagihara, or SH, reaction) is a versatile method of synthesis for acetylenic compounds, which are rapidly gaining importance as advanced new materials and building blocks for implementing unusual molecular architectures. 

Cross-coupling Polymerization at sp-Hybridized Carbons 11.19.3.1 Polymerization by Sonogashira-Hagihara Coupling... 

Alkynylsilane Cross-Couplings-The Sila-Sonogashira-Hagihara Reaction... 

Significantly higher yields were, however, achieved in the absence of a Pd catalyst for this procedure and hence sparked interest in Pd-free variants of the sila-Sonogashira-Hagihara reaction. A simple, but efficient system used the inexpensive and readily available CuCl/PPhj combination for the catalytic cross-coupling of alkynylsilanes with aryl iodides [322]. 

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