Palladium-catalyzed coupling of vinyl triflates with organostannanes. Synthetic and mechanistic studies

Journal Article · Wed May 28 00:00:00 EDT 1986 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00271a037· OSTI ID:5455974

Scott, W J; Stille, J K

The palladium-catalyzed coupling reaction of vinyl triflates with acetylenic, vinyl, allyl, and alkyl tin reagents in the presence of lithium chloride or another suitable salt takes place in high yields under mild reaction conditions; however, benzyl and phenyl tin reagents give poor yield of coupled product. The utilization of a tin or silicon hydride reagent in place of the organotin partner yields the alkene by reductive cleavage of the triflate group. The palladium-catalyzed reaction of vinyl triflates with hexamethylditin gives vinyl stannanes in high yields. Regioselectively formed vinyl triflates can be used to produce 1,3-dienes as the regioisomeric coupled products.

• Research Organization: Colorado State Univ., Fort Collins
• OSTI ID: 5455974
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 108:11; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALI METAL COMPOUNDS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
DATA
ELEMENTS
EXPERIMENTAL DATA
FLUORINATED ALIPHATIC HYDROCARBONS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
INFORMATION
LITHIUM CHLORIDES
LITHIUM COMPOUNDS
LITHIUM HALIDES
METALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANOMETALLIC COMPOUNDS
PALLADIUM
PLATINUM METALS
SULFONATES
TIN COMPOUNDS
TRANSITION ELEMENTS
YIELDS