Palladium-catalyzed coupling, of vinylic

PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES 4-tert-BUTYL-l-VINYLCYCLOHEXENE and l-(4-tert-BUTYLCYCLOHEXEN-l-YL)-2-PROPEN-l-ONE... 

Ma et al. demonstrated that the palladium-catalyzed coupling of vinyl halides 60 and allenyl/propargyl metal species 59 can deliver vinyl allenes 61 [40],... 

Most Williamson reactions proceed by the 8 2 mechanism, but there is evidence (see p. 446) that in some cases the SET mechanism can take place, especially with alkyl iodides. Secondary alcohols have been converted to the corresponding methyl ether by reaction with methanol in the presence of ferric nitrate nonahy-drate. Vinyl ethers have been formed by coupling tetravinyl tin with phenols, in the presence of cupric acetate and oxygen. " The palladium-catalyzed coupling of vinyl triflates and phenols has also been reported. ... 

Stifle, J. Palladium-catalyzed coupling of vinyl tri-flates with organostannanes A short synthesis of pleraplysillin-1. J. Am. Chem. Soc. 1984, 106, 4630 632. 

Coupling of vinyl halides with allyl alcohols,6 Palladium-catalyzed coupling of vinyl halides with allylic alcohols under usual Heck conditions results in a complex mixture of products. Addition of silver carbonate and a phase-transfer catalyst can result in a palladium-catalyzed coupling of vinyl halides with a primary allylic alcohol to give a -y.S-enal, with retention of configuration of the vinyl halide. 

PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES 4-tert-BUTYL-l-... 

The palladium-catalyzed coupling of vinyl triflates with amides, carbamates, and sulfonamides has been reported by researchers at Merck.119 They identified Xantphos as the best ligand for this reaction. The product enamides serve as valuable synthetic intermediates as they can undergo asymmetric hydrogenation to give enantiopure amines. 

PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES 4-tert-BUTYL-l-VINYLCYCLOHEXENE AND l- 4-tert-BUTYLCYCL0HEXEN-l-YL)-2-PR0PEN-l-0HE (Cyclohexene, 4-(l.l-dieiethylethyl)-l-ethenyl- and 2-Propen-l-one, l-[4-(l.l-dlMethy1ethy1)-l-cyclohexen-l-yI)... 

R Palladium Catalyzed Coupling of Vinyl Triflates with... 

Application of carbon-carbon cross-coupling/67C-electrocyclization cascade reactions in pyridine synthesis is well known. Larock and coworkers developed a palladium-catalyzed coupling of vinylic imines 279 with terminal alkynes 280 followed by subsequent copper-catalyzed cyclization of 281 to give aryl, vinyl, and alkyl-substituted pyridines 282 in moderate yields. ... 

X. Zhang, R. C. Larock, Org. Lett. 2003, 5, 2993-2996. Synthesis of highly substituted 1,3-dienes and 1,3,5-trienes by the palladium-catalyzed coupling of vinylic halides, internal alkynes, and organoboranes. 

SCHEME 637 Palladium-catalyzed coupling of vinyl halides with pinacolborane [51]. 

Larock RC, Yang H. Synthesis of pyrrolidines and piperidines via palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides. J. Org. Chem. 1994 59 (15) 4172 178. 

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