Die Stille-Reaktion ist eine der sehr wenigen Reaktionen, in denen unter milden Bedingungen Kohlenstoff-Kohlenstoff-Bindungen geknüpft werden können. Man verwendet die Reaktion häufig in der Synthese komplizierter Moleküle zur Verknüpfung größerer Molekülbausteine. Die Autoren diskutieren vom präparativen Standpunkt aus Grenzen, Einflüsse, strukturelle Effekte und die Wahl der geeigneten Reaktionsbedingungen. Mit ausführlichen Vorschriften und vielen Beispielen. (11/98)
Die Stille-Reaktion ist eine der sehr wenigen Reaktionen, in denen unter milden Bedingungen Kohlenstoff-Kohlenstoff-Bindungen geknüpft werden können. Man verwendet die Reaktion häufig in der Synthese komplizierter Moleküle zur Verknüpfung größerer Molekülbausteine. Die Autoren diskutieren vom präparativen Standpunkt aus Grenzen, Einflüsse, strukturelle Effekte und die Wahl der geeigneten Reaktionsbedingungen. Mit ausführlichen Vorschriften und vielen Beispielen. (11/98)
VITTORIO FARINA, PhD, is Director at the Boehringer Ingelheim Pharmaceuticals Department of Chemical Development. VENKAT KRISHNAMURTHY, PhD, is a research chemist with Occidental Chemical Corporation. WILLIAM J. SCOTT is a research chemist with the Bayer Corporation Institute of Chemistry, Department of Medicinal Chemistry.
Inhaltsangabe
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.
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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