Palladium catalyzed coupling between aryl

Subsequently, palladium-catalyzed couplings between aryl halides and sulfoximines were also used by Gais, Harmata, and others. For example, see M. Harmata, S. K. Ghosh, Org. Lett. 

Chiral quinolinones can be accessed by the palladium-catalyzed coupling between aryl bromides and /3-amino acids, followed by intramolecular acid-catalyzed cyclisation (Equation 136) <1998TA1137>. The reaction of 2-amino-1,3-diene with quinolinone yields the acridine derivative directly (Scheme 75) <1997J(P1)2807>. 

The first palladium-catalyzed coupling between a secondary amine and an aryl chloride was described by Beller, Hermann and co-workers in 1997 [70]. Use of palladacycle 12 as catalyst resulted in C-N bond formation in good yield for several secondary amines and electron-deficient aryl chlorides, Eq. (40). In these transformations, varying amounts of the regioisomeric product was observed, indicative that to some degree the reaction proceeds via a benzyne intermediate. 

Palladium-catalyzed coupling between halogenated nucleosides and ar-ylstannanes containing a boronic acid substituent (see below) in the aryl group proceeds chemoselectively at the C—Sn bond rather than at the C—B bond to give boron-containing nucleosides (166). The methodology... 

Besides the study on Suzuki cross-coupling reactions (Scheme 5) in the ionic liquid 1,3-di-n-butyl-imidazolium tetrafluoroborate ([BBIM][BF4]) catalyzed by palladium prepared in situ in a cleaning bath, Srinivasan and co-workers reported ligand-free Pd-catalyzed couplings between aryl halides and terminal alkyne ... 

The alkaloid dubamine contains a single bond between the two heteroaiene units. This iond was formed in 79% yield by the generally valuable palladium-catalyzed coupling of an ryltrimethylstannane with an aryl triflate (see section 1.6). The requisite stannane was prepared from l,3-benzodioxol-5-yl triflate and hexamethykfistannane with the same palladium atalyst, the triflate ester was obtained from 2(lff)-quinolinone and trifluoromethanesulfonic. nhydride (A.M. Echavarren, 1987). An earlier attempt to perform this aryl coupling by dassical means gave a yield of only 1 %. 

The palladium-catalyzed C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base is referred as the Heck Reaction . Recent developments in the catalysts and reaction conditions have resulted in a much broader range of donors and acceptors being amenable to the Heck Reaction. 

Thienoisoquinolines can be prepared in high yields by the palladium cross-coupling reaction of o-formylarylboronic acids with aryl halides. By this method, thieno[3,2-c]- (102), thieno[3,4-c]-(103), and thieno[2,3-c]isoquinolines (104) have been prepared in yields of 90%, 52%, and 75%, respectively (Scheme 48) <86CS3il, 89JHC865). This method was unsuccessful for the preparation of thieno[3,2-c]quinoline A-oxide and thieno[3,2-c]isoquinoline A-oxide. The former compounds were readily prepared via a modification of the reaction using a palladium-catalyzed coupling reaction between 2-tributylstannyl-3-thiophenecarboxaldehyde and o-bromonitrobenzene, while the isoquinoline A-oxide was prepared by mcpba oxidation of the parent compound <90JHC1127>. 

Equally useful palladium-catalyzed coupling reactions between aryl halides and aryl organometallics have been developed, in which the latter component is usually either a trialkylstannane derivative or the corresponding arylzinc chloride species. In contrast to the foregoing nickel-mediated couplings with... 

Various carbon-carbon cross-coupling reactions are employed to arrive at oligomers from fluorene monomers, including nickel-cataylzed Yamamoto coupling between aryl halides [48], palladium(0)-catalyzed Suzuki coupling between boronic acids/esters and halides [49], and ferric-chloride-catalyzed Scholl reaction, also called Friedel-Crafts arylation, of bare fluorenes [50,51]. 

---