Stille Coupling

Definition:

Palladium-catalyzed cross coupling reaction of organostannanes with organic halides, acetates or perfluorinated sulfonates lacking a sp³-hybridized ß-hydrogen:

Frequency of appearance:

        This bar graph represents all of the online articles that were found to contain this specific name reaction in the title of the article. Tetrahedron letters, Tetrahedron, Synthetic letters, Synthesis, Journal of Organic Chemistry and Journal of the American Chemical Society are represented here. This table by no means represents the periodicity of the name reaction found in the literature.

Original references:

1. M. Kosugi et al., Chem. Letters 1977, 301 (1977).
2. D. Milstein, J. K. Stille, J. Am. Chem. Soc. 100, 3636 (1978).

Recent academic references:  Click here for more references

3. Total synthesis of (+)-Phorboxazole A

• Smith, A. B, III; Verhoest, P. R.; Minbiole, K. P.; Schelhaas, M.; J. Am. Chem. Soc.; 2001; 123(20); 4834-4836.

4. Preparation and reactions of 3,4-Bis(tributylstannyl)-2(5H)-furanone

• Mabon, R.; Richecour, A. M. E.; Sweeney, J. B.; J. Org. Chem.; 1999; 64(2); 328-329 

5. Development of a One-Pot Palladium-Catalyzed Hydrostannylation/Stille Coupling Protocol with Catalytic Amounts of Tin

• Maleczka, R. E., Jr.; Terstiege, I.; J. Org. Chem.; 1998; 63(26); 9622-9623.

6. http://www.iupac.org/publications/pac/1999/71_06_pdf/nicolaou.pdf

Recent process references:

                                                        N/A

Mechanism:

Scope and Limitations:

• Pd = Pd(PPh₃)₄, PhCH₂Pd(PPh₃)₂Cl
• R = alkynyl, alkenyl, aryl, allyl, benzyl, alkyl
• R' = acyl, alkenyl, allyl, benzyl, aryl
• X = Cl, Br, I, OCOCH₃
• Olefins usually retains its geometry. ^A
• Can be done in aqueous KOH. ^B

Synonyms: