1,2-Additions to heteroatom-substituted olefins by organopalladium reagents

Abstract

ChemInform Abstract (114 refs.).

Heck Reaction—State of the Art

“…A review by Daves and Hallberg [53] highlights typical heteroatom-substituted olefins to organopalladium reagents, where a new carbon-carbon bond is formed via 1,2-addition of an organopalladium species to the often strongly polarized carbon-carbon double bond of a heteroatom substituted olefin. These types of reactions afford versatile and efficient synthetic routes to a wide variety of compounds.…”

Ligand‐Free Pd‐Catalyzed Highly Selective Arylation of Allylic Esters with Retention of the Traditional Leaving Group

“…[2] Over the past several decades, the scope of the Heck reaction has been expanded significantly to include aryl chlorides [3] and tosylates, [4] alkyl halides, [5] and arenes (through C À H activation) as suitable substrates.…”

“…Competitive processes in the Pd-catalyzed reaction of iodobenzene and allyl acetate. [e] Pd(OAc) 2 Ag 2 CO 3 (0.6) toluene 24 67 9 [e] Pd(OAc) 2 Ag 2 CO 3 (2.0) toluene 24 18…”

“…11 [e] Pd(OAc) 2 Ag 2 CO 3 (0.6) K 2 CO 3 toluene 24 < 5 12 [e] Pd(OAc) 2 AgNO 3 (1.2) toluene 24 0 13 [e] Pd(OAc) 2 AgNO 3 (1.2) K 2 CO 3 toluene 16 35 14 [e,f ] Pd(OAc) 2 Ag 2 CO 3 (0.6) toluene 24 32…”

Palladium-Induced Intramolecular Coupling Reactions of Some Alkenyl(o-iodobenzyl)silanes

“…An important tool for this type of reactions is provided by the intermolecular as well as the intramolecular Heck-type cross-coupling reactions with Pd 0 and Pd II complexes as very efficient catalysts [2]. More recently, the potential of organosilicium compounds in cross-coupling reactions has been explored [3] [4]. Thus, iodoarenes and 1-iodoalkenes react with trimethyl(vinyl)silane in the presence of [{PdCl(h 3 -C 3 H 5 )} 2 ] as catalyst after activation of the silane with naked F À ions to give vinylarenes and -dienes, respectively.…”