Coupling is a versatile C-C bond forming reaction between stannanes and
halides or pseudohalides, with very few limitations on the R-groups.
Well-elaborated methods allow the preparation of different products from
all of the combinations of halides and stannanes depicted below. The
main drawback is the toxicity of the tin compounds used, and their low
polarity, which makes them poorly soluble in water. Stannanes are
stable, but boronic acids and their derivatives undergo much the same
chemistry in what is known as the Suzuki Coupling. Improvements in the
Suzuki Coupling may soon lead to the same versatility without the
drawbacks of using tin compounds.
Convenient electrophiles and stannanes:
Mechanism of the Stille Coupling
Stille Coupling Made Easier - The Synergic Effect of Copper(I) Salts and the
S. P. H. Mee, V. Lee, J. E. Baldwin, Angew. Chem. Int. Ed., 2004,
Efficient Stille Cross-Coupling Reaction Catalyzed by the Pd(OAc)2/Dabco
J.-H. Li, Y. Liang, D.-P. Wang, W.-J. Liu, Y.-X. Xie, D.-L. Yin, J. Org.
Pd(PPh3)4-PEG 400 Catalyzed Protocol for the Atom-Efficient Stille
Cross-Coupling Reaction of Organotin with Aryl Bromides
H. Huang, H. Jiang, K. Chen, H. Liu, J. Org. Chem., 2009,
Palladium/Imidazolium Salt Catalyzed Coupling of Aryl Halides with
G. A. Grasa, S. P. Nolan,
Org. Lett., 2001, 3, 119-122.
Stille Couplings Catalytic in Tin: A "Sn-F" Approach
R. E. Maleczka, W. P. Gallagher, Org. Lett., 2001, 3,
Highly chemoselective coupling of allenylstannanes with organic iodides
promoted by Pd(PPh3)4/LiCl: an
efficient method for the synthesis of substituted allenes
C.-W. Huang, M. Shanmugasundaram, H.-M. Chang, C.-H.
Cheng, Tetrahedron, 2003, 59, 3635-3641.
Palladium-Catalyzed Coupling of Allylic Acetates with Aryl- and
L. Del Valle, J. K. Stille, L. S. Hegedus, J. Org.
Chem, 1990, 55, 3019-3023.
Palladium-Catalyzed Chemoselective Cross-Coupling of Acyl Chlorides and
R. Lerebours, A. Camacho-Soto, C. Wolf, J. Org. Chem., 2005, 70, 8601-8604.
Synthesis of Carotenoids
and Retinoids: Novel Approaches involving the Stille Reaction as a Key Step