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Sulfones, alkenyl coupling reactions

Table 5.3 Iron catalyzed cross-coupling reactions of alkenyl sulfonates. Table 5.3 Iron catalyzed cross-coupling reactions of alkenyl sulfonates.
Scheme 5.4 Iron-catalyzed cross-coupling reaction of alkenyl sulfones developed by Julia and coworkers. Scheme 5.4 Iron-catalyzed cross-coupling reaction of alkenyl sulfones developed by Julia and coworkers.
Derivatives of sulfonic acids such as the IV-phenylbisimide of trifluoromethane-sulfonic acid (examples Figure 13.23, Side Note 13.3 and Figure 16.2). Note that alkenyl tri-flates are obtained in this way and these are the substrates of a variety of Pd-mediated C,C-coupling reactions (Chapter 16). [Pg.540]

The oxidative addition of organic electrophiles (halides, sulfonates, and related activated compounds) to palladium(O) is the first step in the cross-coupling and Heck reactions. Much work has been done on the mechanisms of the oxidative addition reactions of aryl and alkenyl halides and triflates (C(sp )-X electrophiles) [65], the most common organic electrophiles in cross-coupling reactions. [Pg.3]

Another feasible combination for iron-catalyzed cross-coupling reactions is those of functionalized arylcopper reagents as nucleophiles with alkenyl sulfonates as electrophiles. Tris(acetylacetonato)iron (10 mol%) functions as a precatalyst in this system that tolerates ester or cyano groups. The required arylcopper reagents can be prepared from the corresponding Grignard reagents by treatment with copper(I) cyanide di(lithium chloride) (Scheme 4—217). ... [Pg.683]

In addition to the cross-coupling reactions of alkyl halides or sulfonates with organometallic nucleophiles, the former can also directly undergo C-C bond formation with nonactivated C-H bonds of alkenes or arenes in a Heck-type reaction. Iron-catalyzed intramolecular dehydrohalogenation of 2-iodoethanal alkenyl acetals with phenyl-magnesium bromide in the presence of a catalytic amount of iron(II) chloride provides tetrahydrofliran derivatives in moderate yields (Scheme 4-240). Allyl 2-halophenyl ethers provide dihydrobenzofiiran derivatives under these conditions. ... [Pg.696]

The traditional scope for this reaction involved coupling alkenyl or aryl iodides or bromides with aryl, alkenyl, or alkynylzinc halides. However, recent modifications have allowed the scope to be extended to include additional electrophiles see Electrophile) such as aryl and vinyl chlorides, sulfonate esters, aryl ethers, and substrates with... [Pg.5646]

Alkenylsilanes. Addition of (MesS sSiH to 1-alkynes in the presence of a Rh(I) complex furnishes the ( )-l-silylalkenes, whereas the (Z)-isomers are obtained from formal group exchange reaction starting from (Z)-l-alkenyl sulfones. These alkenylsilanes can be used in Hiyama coupling after treatment with alkaline H2O2. [Pg.469]


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