Suzuki-Miyaura coupling reaction synthesis

In this study we show that the Pd/C catalyzed Suzuki-Miyaura coupling reaction can be performed in a microwave oven. Overall the microwave synthesis is faster than comparable thermal methods and the combination of the ease of use of the microwave oven and the facile work-up with Pd/C makes this a very efficient method for performing coupling reactions. 

This chemistry features in a synthesis of the left hand fragment of yessotoxin and adriatoxin <02OL3943>. Assembly of the F-N ring component of gymnomycin A, involves a b-alkyl Suzuki-Miyaura coupling reaction <02OL1747>. 

An efficient, diverse synthesis of oxazolo[4,5-c]quinoline-4-ones and thiazolo[4,5-c]quinolines-4-ones is carried out in two steps from readily available starting materials <03OL2911>. The Suzuki-Miyaura coupling reaction was employed. 

A highly regioselective microwave promoted synthesis of 2-aryl-6-chloro-benzothiazoles (xxxviii) by the Suzuki-Miyaura coupling reaction of 2,6-dic-hlorobenzothiazole with arylboronic acids is given by Heo et al. [58]. 

Heo Y, Song YS, Kim BT et al (2006) A highly regioselective synthesis of 2-atyl-6-chlorobenzothiazoles employing microwave-promoted Suzuki-Miyaura coupling reaction. Tetrahedron Lett 47 3091-3094... 

Suzuki-Miyaura coupling, involving the reaction of aryl boronic derivatives with aryl halides in the presence of a palladium catalyst, is a very powerful method for the preparation of biaryls. Solutions of aryl bromides or iodides supported on onium salts via an ester link in an RTIL lead to BTSILs that can be engaged in the Suzuki-Miyaura coupling reaction with aryl boronic derivatives. like the Heck reaction, this coupling is also sensitive to the variations in different parameters. The possibility to synthesize libraries of biarylic derivatives by parallel synthesis is illustrated by (Scheme 5.5-39) [51]. 

Suzuki-Miyaura Coupling. The Suzuki-Miyaura coupling reaction is very useful for construction of carbon-carbon bonds under mild conditions. Because it is tolerant of many functional groups, it has been employed widely in the synthesis of many natural products and related compounds. The stereochemistry of such coupling reactions proceeds with retention of configuration at both the C-X and C-(9-BBN) centers, confirmed recently hy independent studies from the groups of Woerpel and Soderquist. ... 

A one-pot, four-component Suzuki—Miyaura coupling reaction for the synthesis of EDOT-organic dyes was carried out and their photovoltaic properties studied (14T8690). 

Yang X, Don X, Mullen K (2008) Efficient synthesis of symmetrically and unsymmetrically substituted hexaphenylbenzene analogues by Suzuki-Miyaura coupling reactions... 

Recently, the synthesis of palladium complexes based on 1,8-naphthridine functionalized NHC motif has been reported [16]. This was the first reported case of the successful preparation of a di-palladium complex with double 1,8-naphthridine-based NHC ligands (12). It was reported to catalyze Suzuki-Miyaura coupling reactions for aryl bromides imder refluxing temperatures but was found to be ineffective for activated or unactivated aryl chlorides. 

Frechet and coworkers reported the synthesis of a dendrcm-modified polythiophene, in which one terminus of P3HT was linked to the focal point of a polyester-type dendron (Scheme 55) [153]. Introduction of the benzylamine moiety to the end group of polythiophene was carried out by the Suzuki-Miyaura coupling reaction of the polythiophene with the H/Br end groups and the corresponding boronic acid hydrochloride. The amino-functionalized polythiophene was then... 

Table 6 Stereoselective synthesis of trisubstituted fluoroalkenes by Suzuki-Miyaura coupling reaction using (fluoroafkenyl)boronates 79...

A facile synthesis of some new substituted aryl and heteroarylflavones by thermal and microwave-assisted Suzuki-Miyaura coupling reaction was also carried out (Joshi and Hatim, 2012). 

The Stille reaction has developed as a popular protocol for the formation of C-C bonds due to the air- and moisture-stability as well as functional group compatibility of organotin compounds. Together with the Suzuki-Miyaura coupling it is one of the most powerful methods for the synthesis of molecules containing unsymmetrical biaryl moieties. However, despite its efficiency, this versatile reaction has slowly been displaced by other procedures that avoid the use of highly toxic organostannanes. 

An interesting polymer-assisted variant of the Suzuki-reaction was recently disclosed by Vaultier and coworkers (Scheme 17) [43]. Aryl boronic acids can be immobilized on an ion exchange resin. Under Suzuki-Miyaura coupling conditions bisaryl species are released into solution and isolated with minimum purification. The authors also demonstrated that this strategy can be employed for the synthesis of macroheterocycles. 

The same group reported on a library synthesis of 3-aminoimidazo[l,2-a]-pyridines/pyrazines by fluorous multicomponent reactions. Here the overall yields, as well as the yields for the separate Suzuki-Miyaura reactions that were a part of the synthesis, were relatively low due to competing reactions and the poor reactivities of the substrates, but the speed of the microwave-mediated syntheses and ease of separation underlined the usefulness of fluorous reagents [140]. A recent paper further illustrated the use of Suzuki-Miyaura couplings of aryl perfluorooctylsulfonates in the decoration of products derived from 1,3-dipolar cycloadditions [141]. 

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