The Stille Reaction, 38 Years Later
2015/04/17 by Carlos Cordovilla, Camino Bartolomé, Jesús M. Martínez‐Ilarduya +1 · 2 citations
Chemistry · #Asymmetric Hydrogenation and Catalysis #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods
paper · doi:10.1021/acscatal.5b00448
openalex publication_date 2015/04/17 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01
Abstract
The first now-named Stille reaction was published 38 years ago, and the last comprehensive revision of this catalysis was in 2004. Since then, the knowledge of the different steps of the three possible (and sometimes competing) reaction pathways (cyclic, open, and ionic) has been almost completed by synergistic experimental and theoretical studies: the Stille reaction is perhaps the best characterized catalytic process if we consider the number of intermediates that have been detected. This review concentrates on the mechanistic new knowledge and on important aspects such as the revolution with the use of bulky phosphines, the bimetallic alternative of the Stille reaction, the enantioselectivity in Stille and palladium-free Stille processes, the meaning of copper effect, or the possible approaches to make Stille coupling a greener process.
Citations
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]
- Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications
- A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium
- On the Configuration Resulting from Oxidative Addition of RX to Pd(PPh3)4 and the Mechanism of the cis-to-trans Isomerization of [PdRX(PPh3)2] Complexes (R = Aryl, X = Halide)
- Mechanism of the Stille Reaction. 2. Couplings of Aryl Triflates with Vinyltributyltin. Observation of Intermediates. A More Comprehensive Scheme
- The Mechanisms of the Stille Reaction
- Reactions of organic halides with R3 MMR3 compounds (M = Si, Ge, Sn) in the presence of tetrakis(triarylphosphine)palladium
- Theoretical Insight into the C−C Coupling Reactions of the Vinyl, Phenyl, Ethynyl, and Methyl Complexes of Palladium and Platinum
- REACTIONS OF ALLYLTIN COMPOUNDS III. ALLYLATION OF AROMATIC HALIDES WITH ALLYLTRIBUTYLTIN IN THE PRESENCE OF TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(O)
- ALKYLATION, ARYLATION, AND VINYLATION OF ACYL CHLORIDES BY MEANS OF ORGANOTIN COMPOUNDS IN THE PRESENCE OF CATALYTIC AMOUNTS OF TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(O)
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