The Stille reaction /

Bibliographic Details
Main Author: Farina, Vittorio
Other Authors: Krishnamurthy, Venkat, Scott, William Johnston
Format: Printed Book
Language:English
Published: New York : J. Wiley, c1998.
Subjects:
Stille reaction.
Online Access:http://www.loc.gov/catdir/bios/wiley041/98039154.html
http://www.loc.gov/catdir/description/wiley032/98039154.html
http://www.loc.gov/catdir/toc/onix02/98039154.html
Table of Contents:
  • Mechanistic considerations, regiochemistry and stereochemistry.
  • Scope and limitations: the electrophile.
  • Alkenyl Halides.
  • Aryl and Heterocyclic Halides.
  • Acyl Chlorides.
  • Allylic, Benzylic, and Propargylic Electrophiles.
  • Alkenyl Sulfonates and Other Electrophiles.
  • Aryland Heterocyclic Sulfonates and Other Derivatives.
  • Miscellaneous Electrophiles.
  • Scope and limitations: the stannane.
  • Alkylstannanes.
  • Alkenylstannes.
  • Aryl and Heterocyclic Stannanes.
  • Alkynylstannanes.
  • Allylstannanes.
  • Other Stannanes.
  • Carbonylative couplings.
  • Alkenyl Halides.
  • Aryl and Heterocyclic Halides.
  • Allylic and Benzylic Halides.
  • Alkenyl Sulfonates.
  • Aryl and Heterocyclic Sulfonates.
  • Miscellaneous Substrates.
  • Complex synthetic sequences involving tin-to-palladium (ii) metathesis steps.
  • Side reactions.
  • Homocoupling Reactions.
  • Transfer of "Nontransferable" Ligands.
  • Destannylation.
  • Cine Substitution.
  • Phosphorus-to-Palladium Aryl Migration.
  • Electrophile Reduction.
  • Product Isomerization.
  • Miscellaneous Side Reactions.
  • Comparison with other methods.
  • Experimental conditions.
  • The Stannane: Preparation and Handling.
  • Alkenyl and Aryl Triflates.
  • Choice of Nontransferable Ligands.
  • Choice of Catalyst and Ligands.
  • Choice of Solvent.
  • Additives.
  • Workup: Removal of Tin Halides.
  • Experimental procedures.
  • Trimethyl([3-(Cyclohexen-1-yl)-2-Propynyl)silane [Cross-Coupling of a Vinyl Halide with an Alkynylstannane Using Pd(PPh_3)_2Cl_2].
  • 4-tert Butyl-1-Vinylcyclohexene [Cross-Coupling of a Vinyl Triflate with a Vinylstannane Using Pd(PPh_3)_4 and LiCl].
  • 1-(4-Methoxyphenyl)-4-tert-Butylcyclohexene [Cross-Coupling of a Vinyl Triflate with an Arylstannane Using Pd_2(dba)_3 and AsPh_3].
  • 3-Methyl-2-(4-Tolyl)-2-Cyclopentenone [Cross-Coupling of an Unreactive Alkenyl Halide under "Modified" Conditions Using Pd(PhCN)_2Cl_2 AsPh_3, and Cul as Cocatalyst].
  • 1-(4-Nitrophenyl)-2-Propenone (Cross-Coupling of an Acid Chloride with an Arylstannane).
  • 4-Allylacetophenone [Cross-Coupling of an Aryl Triflate under Mild Conditions using Tri(2-Furyl)Phosphine as Ligand.
  • 8-(Trimethylstannyl)Quinoline (Preparation of an Arylstannane by Cross-Coupling and Aryl Triflate with Hexamethyldistannane).
  • 4-(tert-Butyl-1-Vinylcyclohexen-1-Yl)-2-Propenone [Carbonylative Cross-Coupling of an Alkenyl Triflate with an Alkenylstannane using Pd(PPh_3)_4 and LiCl].
  • (E)-1-(4-Methoxphenyl)-3-Phenyl-2-Propenone [Carbonylative Cross-Coupling of an Aryl Triflate with an Alkenylstannane using Pd(dppf)Cl_2 and LiCl].
  • Tubular survey.
  • Tables.
  • References.

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