Suzuki-Miyaura coupling advantages

A major advantage of this MCR is that organoboronic acids are readily available in a large variety of structural configurations and they can be formed in isomeri-cally pure forms. As a result of their widespread utility in Suzuki-Miyaura coupling [27, 28] and other reactions [29, 30], a variety of aryl and heteroaryl [31] boronic adds are now commercially available and can be employed in this MCR process. Most of these compounds are also air and water stable as well as non-toxic and environmentally friendly. They also tolerate many functional groups, thereby... 

To conclude, we should mention the work similar, in essence, in which thienyl-boronic acids or pinacol esters react with 1,2-dichlorohexafluorocyclopentene via the Suzuki-Miyaura coupling [111]. A doubtless advantage of the method is its applicability to various substrates bearing reactive functionalities such as cyano and ester moieties, which cannot be compatible nnder the conventional diarylethene synthesis conditions using organolithium reagents. 

We conclude that the addition of phosphanes to palladium(II)-NHC complexes is advantageous with respect to reaction times, yield and completion ratio for a wide range of catalytic coupling reactions including Tsuji-Trost, allylic amination, Suzuki-Miyaura, Heck and Stille. 

Suzuki-Miyaura cross-coupling polymerization of 1,4-bis((Z)-2-bromovinyl)benzenes with aryl-bis-boronic acids. The interest has been in an alternative approach, where rather than building a PPV with a pre-ordained stereochemistry, a postpolymerization yyn-selective reduction on a poly(phenylene ethynylene) (PPE) is used [125]. This scheme has the advantage that high molecular weight PPEs can be synthesized using either Pd-catalysis or alkyne metathesis. This route could also potentially allow for the access to an additional array of PPVs that are uniquely accessible from PPEs. The transformation of the triple bonds in PPEs and other acetylene building blocks to alkenes has considerable potential. 

Arylation of a wide range of NH/OH/SH substrates by oxidative cross-coupling with boronic acids in the presence of catalytic cupric acetate and either triethyl-amine or pyridine at room temperature in air. The reaction works for amides, amines, anilines, azides, hydantoins, hydrazines, imides, imines, nitroso, pyrazi-nones, pyridones, purines, pyrimidines, sulfonamides, sulfinates, sulfoximines, ureas, alcohols, phenols, and thiols. It is also the mildest method for NIO-vinylation. The boronic acids can be replaced with siloxanes or starmanes. The mild condition of this reaction is an advantage over Buchwald-Hartwig s Pd-catalyzed cross-coupling. The Chan-Lam C-X bond cross-coupling reaction is complementary to Suzuki-Miyaura s C-C bond cross-coupling reaction. 

Carboxylates Among various 0-substituted electrophiles, O-acylated phenols share a few distinct advantages over other pseudohahdes (i) they are readily available and affordable, (ii) they are relatively stable substrates to various reaction conditions, and (iii) they can serve as directing groups for aromatic substitution reactions such as directed ortho-metallations (DoMs) [58]. Moreover, these carboxylates are much more environmentally friendly, generating acetate salts as the only by-product in the Suzuki-Miyaura cross-coupling reaction [59,... 

Practical advantages and disadvantages of the Suzuki-Miyaura protocol over other Ar-Ar cross-coupling methods to be discussed are generally appreciated by synthetic chemists (Table 14.2). Nevertheless, this cross-couphng reaction, as... 

To avoid the aforementioned instability issues associated with the pyridine-boronic acid derivatives, at least in the context of DMG-containing systems, a general one-pot DoM-Suzuki-Miyaura cross-coupling procedure has been developed for the production of various functionalized azabiaryls. It takes advantage of the use of triisopropylborate as an in situ boron electrophile for LDA-mediated DoM (Table 14.8). Except for the electron-rich aryl bromides (entries 3, 6, and 9), reasonable yields of cross-coupling products are obtained [25aj. 

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