Aryl halides organometallic compound cross-coupling

Organometallic reagents and catalysts continue to be of considerable importance, as illustrated in several procedures CAR-BENE GENERATION BY a-ELIMINATION WITH LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE l-ETHOXY-2-p-TOL-YLCYCLOPROPANE CATALYTIC OSMIUM TETROXIDE OXIDATION OF OLEFINS PREPARATION OF cis-1,2-CYCLOHEXANEDIOL COPPER CATALYZED ARYLA-TION OF /3-DICARBONYL COMPOUNDS 2-(l-ACETYL-2-OXOPROPYL)BENZOIC ACID and PHOSPHINE-NICKEL COMPLEX CATALYZED CROSS-COUPLING OF GRIG-NARD REAGENTS WITH ARYL AND ALKENYL HALIDES 1,2-DIBUTYLBENZENE. 

Another, mechanistically closely related reaction is the cross-coupling reaction of aryl, benzyl, vinyl, or allyl halides with organometallic coupling reactions, such as Grignard reagents or, preferably, less reducing organometallics such as tin compounds or boronic acids RB(OH)2 the latter allow the reaction to be conducted even in aqueous media.83 The principal reaction steps are ... 

The formation of unsymmetric biaryls via catalytic cross-coupling of aryl halides and organometallic compounds has been shown to proceed in ionic liquids with enhanced activity. The Suzuki-Miyaura cross coupling (cf. Section 2.11)... 

CROSS-COUPLING REACTIONS BETWEEN ORGANOMETALLIC REAGENTS AND VINYL, ARYL AND ALKYNYL HALIDES AND RELATED COMPOUNDS... 

Oxidative addition of aryl (or vinyl) halide to Pd(0) precursor forms the monoarylpalladium complex that is the common intermediate in the catalytic cross-coupling reactions of haloarene with organometallic compounds of main group elements such as Mg, Si, and Sn. Alkynylcopper, formed from alkyne, Cu(I) salt and base in the reaction mixture, transfers the ligand to the above Pd complex, giving an intermediate complex with aryl (or vinyl) and alkynyl ligands bonded to Pd. Reductive elimination of arylacetylene (or enyne) occurs... 

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