Examples of the Suzuki Coupling Reaction

We will provide a class of low bandgap polymers applied in BHJ PSCs that are synthesized by Suzuki polyeondensation. This section cannot possibly cover all these different polymers. Emphasis will be placed upon important classes of conjugated polymers based on bridged phenylenes, for example poly(2,7-fluorene), poly(2,7-earbazole), and poly(2,7-dibenzosilole) based D-A conjugated polymers. 

In 2003, Svensson et al. reported a low bandgap polymer, P , and its application in PSCs. Pi, was synthesized by Suzuki polyeondensation of 

Similarly, Blouin et al. reported the synthesis of P20 by Suzuki coupling of 

Bo et al reported the synthesis of a series of D-A alternating conjugated polymers P24-31 with 5,6-bis(octyloxy)benzothiadiazole as the acceptor unit by Suzuki polyeondensation of dibromo monomers and 5,6-bis(octyloxy)benzo-thiadiazole based diboronic acid pinacol ester. P24) with a of 102 kg mol and a PDI of 1.66, gave a PCE of 5.08% in devices with P24 PC7iBM as the active 

Polymer solar cells based on P29 and PC71BM demonstrate aPCE of 4.8%. P30, with 9-alkylidene-9//-fluorene as the donor unit and 5,6-bis(octyloxy) benzothiadiazole as the acceptor unit, is of planar structure. PSCs with a blend of P3 and PC71BM as the active layer demonstrate a PCE of 6.2%. P3J, 

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The procedures described in Chapters 4-7 all relate to a set of broadly similar transformations that are becoming exceptionally important and well used in laboratories worldwide. In Chapter 4, eight examples of the Suzuki coupling reaction are described four accounts describe the use on activated alkene (vinyl bromide, triflate or tosylate) as the coupling partner for boronic acid derivatives. The other examples of Suzuki couplings involve aryl bromides and aryl chlorides. It is noteworthy that the methodology introduced by Nolan has been extended to include amination reactions. 

Using the example of the Suzuki-coupling reaction as a common synthesis route for polymeric semiconductors, the economic and ecologic improvements... 

SCHEME 12.31 First example of the Suzuki coupling reaction. 

Use of the Suzuki coupling reaction in the synthesis of PPPs has been reported. For example. Wallow and Novak [31] have polymerized 19 and 20 in the presence of palladium(O) catalyst to generate 21, a water-soluble PPP (Scheme 9). We have... 

A very recent paper described the first examples of asymmetric Suzuki coupling reactions of unactivated alkyl halides.These transformations take advantage of the fact that oxidative addition of secondary alkyl halides to Ni(0) proceeds through radical intermediates. This leads to scrambling of stereochemistry when achiral catalysts are employed, but can be exploited to achieve dynamic kinetic resolution with chiral catalysts. For example, use of a catalyst composed of Ni(COD)2 and chiral 1,2-diamine ligand 55 for the coupling of 52 with 53 gave 54 in 78% yield and 90% ee. 

To the best of our knowledge, the first example of a Suzuki coupling reaction in the synthesis of a PUFA-derived natural product was disclosed in the synthesis of prostaglandin... 

The coupling of 3 4 -methylenedioxyphenyl boronic acid to 7-iodosancycline in the presence of a palladium salt is an example of the Suzuki reaction and is described (1). 

Bromobenzothiazole has also been used as the electrophile in the Suzuki coupling reactions with a variety of structurally diverse boronic acids [36]. Among these examples, derivative 55, a positron emission tomography (PET) probe precursor was produced for the in vivo imaging of Alzheimer s disease. 

The first example of a Suzuki-Miyaura reaction on a pyridopyrimidine skeleton was used for decoration of a 4-diloro[2,3-d]pyrimidin-7(8H)one scaffold. Phe-nylboronic acid was used as a coupling partner with a good isolated yield (Scheme 15.18) [51]. 

The preparation of heterobiaryls, using the Suzuki coupling reaction, has attracted considerable attention, and there are many examples. Using... 

Scheme 7.16. Some examples of the Suzuki reaction. The process permits creation of carbon-carbon bonds by coupling of alkyl, alkenyl, and aryl halides (I > Br Cl) with organoboron compounds. Akira Suzuki, Ei-ichi Negishi and Richard Heck shared the Chemistry Nobel Prize in 2010.

Due to the excellent stereoselectivity of the Suzuki coupling, the reaction has been used in the synthesis of the unsaturated units of a range of natural products. In an example drawn from the synthesis of trisporol B, a dienylic borane and a vinyl iodide are coupled to give the triene 23. ... 

Vinylation can also be done by Pd-catalysed cross-coupling in which one component is used as a halide or triflate and the other as a stannane (Stille reaction) or boronic acid (Suzuki reaction). Entry 9, Table 11.3, is an example of the use of a vinylstannane with a haloindole. lndole-3-boronic acids, which can be prepared by mcrcuration/boration, undergo coupling with vinyl triflates (Entry 10). 

C) [9, 10]. It is said to be the first example of a heated organic reaction performed in a glass chip reactor imder electroosmohc flow (EOF) control [10] (for EOF see [14]). The performance of this reactor for room-temperatare reactions such as the Wittig reaction and Suzuki coupling was demonstrated before. 

This modification proved generally applicable and the Suzuki reaction is arguably the most versatile of modern cross-coupling reactions. The reaction has, for example, attracted the interest of groups involved in high-throughput chemistry, because a large variety of boronic acids are commercially available. 

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