Tris stannane

C Vinyl stannane coupling 9 3-Bromo-l-(methanesulfonyl)indole Pd(OAc)2, chloranil Z-(2-Etho,xy vinyl)tri-n-butylstannane, Pd(PPh3)2Cl2 83 [9]... 

In related work, 3-chloromethylcephems were coupled with tributyl(tnfluoro-vinyl)stannane catalyzed by tri(2-furyl)phosphine palladium(O) [7S, 19] (equation 13). 

Tributyl[( )-l-(methoxymethoxy)-2-butenyl]stannane (4) is available by the addition of tri-butyltin lithium to 2-butenal followed by treatment with chloromethoxymenthane 03. The resulting diastereomers were separated by chromatography to give stereochemically homogeneous a-alkoxystannanes 5 and 6104. 

The readily available organotin compounds include tin hydrides (stannanes) and the corresponding chlorides, with the tri-n-butyl compounds being the most common. Trialkylstannanes can be added to carbon-carbon double and triple bonds. The reaction is usually carried out by a radical chain process,137 and the addition is facilitated by the presence of radical-stabilizing substituents. 

These reactions result in iodine atom transfer and introduce a potential functional group into the product. The trialkylborane method of radical generation can also be used in conjunction with either tri-n-butyl stannane or fnT-(trimethylsilyl)silane, in which case the product is formed by hydrogen atom transfer. 

Table 16-1. Reduction of alcohols with tri- -butyl stannane via imidazole-Y-thionocarboxylates to the corresponding deoxygenated products.

A modification of the azolide method for deoxygenation of alcohols is the conversion of the thiocarbonylimidazolide with methanol into the thionocarbonate, which is then treated with tri-w-butyl stannane/AIBN. Thus, 2,3-dideoxynucleosides (a), (b), and a secodeoxynucleoside (c) have been prepared as follows [52H56]... 

A Water Soluble Tin Hydride Tris(3-(2-methoxyethoxy)-propyl)stannane. 

The preparation of unsubstituted cyclopropenone (7)27,28 was achieved by reducing the readily available tetrachlorocyclopropene (2/)29 with tris(n-butyl)-stannane this produced 3,3-dichloro-AI,2-cyclopropene (22), whose carefully controlled hydrolysis gave rise to a 41—46% yield of pure cyclopropenone, which was stable under an inert gas atmosphere at temperatures below its melting point of -21 °C. 

Tris (dibuty Ibis (2-hydroxy ethylthio)stannane) O-ester with bis(boric acid) XK 4860000... 

Recently, Li successfully conducted the Suzuki and Stille reactions on the pyrazine ring of 3-bromoquinoxalin-2-ylamines [51]. Indolylquinoxaline 92 was obtained from the union of 3-bromoquinoxalin-2-ylamine 90 and l-phenylsulfonyl-2-tri-n-butylstannyl-l//-indole (91). A wide variety of heterocyclic stannanes bearing various functional groups underwent Stille coupling with 90 under the same conditions to give the corresponding adducts in 72-98% yields. 

Butyl(tri-2-pyridyl)stannane can be prepared from 2-lithiopyridine and butyltin trichloride and also from the reaction of 2-lithiopyridine with stannocene. The product acts as a tridentate ligand, and the complexes with Li+ Mo(CO)3, and W(CO)3 have been characterized (Equation (57)). 

The 20-membered all-E tetraene macrolide system 58 was prepared by intramolecular cyclization of vinyl stannane 59 in the presence of tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) and triphenylarsine, as shown in equation 3354. E,E-Dienamines have been... 

Reductive metallation of aldehydes (but not ketones) by tri-n-butyl-(trimethyisilyl)stannane to yield a-hydroxystannanes is catalysed by tetra-n-butylammonium cyanide [15]. Other phase-transfer catalysts are not as effective and solvents, other than tetrahydrofuran, generally give poorer conversions. Use of a chiral catalyst induced 24% ee with 3-phenylpropanal. 

Tris[3-(2-methoxyethoxy)propyl]stannane 2,5,13,16-Tetraoxa-9-stannaheptadecane, 9-[3-(2-methoxyethoxy)propyl]- (12) (130691-03-1)... 

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