Cross-coupling survey

In their cross-coupling survey, Hodgetts showed C2-chlorides, C4-bromides or C5-bromides are competent partners in the Suzuki reaction. Stambuli surveyed bromo- and iodo-oxazoles and found iodooxazoles more reactive in the Suzuki coupling at both the 4- and the 5-position7 ... 

The disclosure of a one-pot directed ortho metalation-boronation and Suzuki-Miyaura cross-coupling of derivatized pyridines 44 to give substituted azabiaryls 45 provided an excellent protocol for the in situ utilization of pyridyl boronic acids whose isolation is known to be difficult <07JOC1588>. The disclosed method relies on the in situ compatibility of LDA and B(Oz-Pr)3 and proceeds in good to excellent yields for the multi-step process. The report details a comprehensive survey of pyridyl boronates and is expected to be of considerable value in the synthesis of bioactive molecules. 

Systematic survey of palladium-or nickel-catalyzed cross-coupling. . 4... 

Although such reactions are strictly not within the scope of this survey, they are included for two reasons firstly they afford compounds which can be used as substrates for the cross-coupling reactions discussed here, and secondly it is possible by the appropriate choice of reaction conditions to carry out two-step, one-pot syntheses. 

The literature has been surveyed up to 1988. Some recent reviews relevant to this section are as follows Ni-, Pd-, " and Cu-catalyzed" coupling reactions. Catalytic asymmetric cross-coupling reactions are not treated in this section, since the subject has recently been well reviewed. ... 

As is evident from Scheme 55, the nucleophilic partner in cross-coupling need not be a phosphine. This section surveys recent results with other P-nucleophiles. 

This review aims to survey the methodologies currently available to perform regioselectively the C2- and C3-arylation of indoles (09AGE9608, 09ASC673, 11PHC(22)1). Our discussion is limited to reactions that are catalyzed by transition metals. Traditional cross-coupling reactions (Scheme 1, Eq. 1) will not be discussed here as this field goes beyond the... 

Recent advances in this area have provided a suite of catalyst options for cross-coupling and addition reaction-g 54,54a,54b a Survey of the literature reveals that choosing the appropriate catalyst and reaction conditions... 

The Suznki reaction is an important C-C bond-forming reaction of an aryl- or vinylboronic acid (112) with an aryl- or vinylhaUde (111, 115), catalyzed by a pal-ladinm(0) complex. Recently, Akira Suzuki won the 2010 Nobel Prize in chanistry for his significant contribution and development of this reaction. The literature survey reveals several modifications to the reaction. The application of various ZnO-supported metal combinations such as Pd-Ag, Pd-Cu, Pd-Ni, and Pd (Kim and Choi 2009) were reported for the cross-coupling Snzuki reaction between aryl halides (111, 115) and phenyl boronic acid (112) (Schemes 9.34, 9.35). These metal combinations with ZnO resulted in excellent yields of the biaryl products. 

This review has been aimed and restricted to provide a noncomprehensive survey of the combined DoM/DreM-cross-coupling reactions for Ar-Ar and various HetAr-bond-forming combinations from which the following aspects may, to various degrees, be appreciated. 

Preprepared (ADC)Pd complexes H2 (Fig. 11.6) was employed [29] as catalyst for the Buchwald-Hartwig amination of aryl halides (for the recent surveys on the Buchwald-Hartwig cross-coupling, see References [62-65]). The obtained results (Scheme 11.13) were compared with those for the structurally related oxyamino- (H4), thioaminocarbene (H5), and the related NHC complex, H14. Catalysts H2, H4, and H5 were efficient in the amination of bromobenzene (yields range from 82% to 92%), demonstrating activities similar to those of the NHC complex H14 (yield 84%). With 2-chloropyridine as the substrate, H2, H4, and H14, allowed the preparation of the target product in a quantitative yield. Catalyst H5 demonstrated a moderate efficiency (yield 47%). 

This radew will focus primarily on recent work not covered by Thomas and Ley, as well as a significant quantity of unpublished work from our laboratories. An account of Chan s original discovery, and Chan and Lam s initial studies will first be presented. The main body of this chapter will involve examination of various types of C-X cross-coupling using boronic adds and their derivatives, as well as mechanistic considerations. Readers are encouraged to >eruse the aforementioned reviews for a more complete survey of the earlier development of this area. 

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