Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides. Synthetic utility and mechanism
Journal Article
·
· J. Am. Chem. Soc.; (United States)
Palladium complexes catalyze the coupling of tetraorganotin compounds with benzyl and aryl halides, benzylchlorobis(triphenylphosphine)palladium(II) (1) being the catalyst of choice. Various functional groups are tolerated by this reaction and generally high yields of the cross-coupled products are obtained. Oxygen has a considerable accelerating effect on the reaction, whereas triphenylphosphine has little effect. The reaction of substituted bromobenzenes with tetramethyltin catalyzed by 1 is accelerated by electron-withdrawing groups; however, a simple Hammett correlation is not observed. Optically active ..cap alpha..-deuteriobenzyl bromide reacts with tetramethyltin to afford optically active ..cap alpha..-deuterioethylbenzene with inversion of configuration. Homocoupling is the main reaction observed when lithium or Grignard reagents react with benzyl chloride under the influence of various palladium catalysts.
- Research Organization:
- Colorado State Univ., Fort Collins
- OSTI ID:
- 5977762
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 101:17; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400302 -- Organic Chemistry-- Isotope Effects-- (-1987)
ALKALINE EARTH METAL COMPOUNDS
CHEMICAL REACTIONS
COMPLEXES
DATA
DATA FORMS
DEUTERIUM
EXPERIMENTAL DATA
GRIGNARD REAGENTS
HYDROGEN ISOTOPES
INFORMATION
ISOLATED VALUES
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
MAGNESIUM COMPOUNDS
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
PALLADIUM COMPLEXES
STABLE ISOTOPES
TIN COMPOUNDS
TRANSITION ELEMENT COMPLEXES
400201* -- Chemical & Physicochemical Properties
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400302 -- Organic Chemistry-- Isotope Effects-- (-1987)
ALKALINE EARTH METAL COMPOUNDS
CHEMICAL REACTIONS
COMPLEXES
DATA
DATA FORMS
DEUTERIUM
EXPERIMENTAL DATA
GRIGNARD REAGENTS
HYDROGEN ISOTOPES
INFORMATION
ISOLATED VALUES
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
MAGNESIUM COMPOUNDS
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
PALLADIUM COMPLEXES
STABLE ISOTOPES
TIN COMPOUNDS
TRANSITION ELEMENT COMPLEXES