Stille—Kelly reaction

Palladium-catalyzed intramolecular cross-coupling reaction of bis-aiyl halides using ditin reagents. 

Bhushan, V. Tetrahedron Lett. 1990, 31,161-164. T. Ross Kelly is a professor at Boston College. 

Mascitti, V. Stille Coupling. In Name Reactions for Homologations-Part / Li, J. J., Ed. Wiley Hoboken, NJ, 2009, pp 133-162. (Review). 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 265, Springer International Publishing Switzerland 2014 

Fukuyama, Y. Yaso, H. Mori, T. Takahashi, H. Minami, H. Kodama, M. Heterocycles 2QQI, 54,259. 

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In Grigg s approach to hippadine (37), he established the connection between the two phenyl rings via the Stille-Kelly reaction [45]. When diiodide 35 was submitted to the Pd(0)/ditin catalyst system, the intramolecular cyclization was realized to establish the C—C bond in lactam 36. Oxidation of the indoline moiety in 36 using 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) then delivered hippadine (37). Analogously, the intramolecular Stille coupling of dibromide 38 led directly to hippadine (37) [46]. 

The Stille reaction is the key step in some synthesis of thiophene-containing condensed heteroaromatics. Enlisting a Stille-Kelly reaction, Iyoda et al. treated dibromide 125 with hexamethylditin in the presence of Pd(Ph3P)4 to afford dithienothiophene (126) [111]. 

Fukuyama, Y., Yaso, H., Mori, T., Takahashi, H., Minami, H., Kodama, M. Total syntheses of plagiochins A and D, macrocyclic bis(bibenzyls), by Pd(0) catalyzed intramolecular Stille-Kelly reaction. Heterocycles 2001, 54, 259-274. 

In Grigg s approach to hippadine (44), the biaryl carbon-carbon bond was generated via a Stille-Kelly reaction [42]. Treatment of 42 with hexamethyl ditin in the presence... 

The Stille-Kelly reaction is rarely used in conjunction with furans. Sessler and coworkers applied this strategy successfully as part of their synthetic pathway for the synthesis of furan-containing porphyrin derivatives. In the presence of hexabutylditin, Pd-catalyzed homocoupling of bromofuran 134 takes place to give bi furan diester 135 [121]. 

The Stille-Kelly reaction is a variant of the Stille coupling where an organodihalide undergoes an intramolecular reaction in the presence of hexamethylditin and a palladium catalyst. 

In particular, hexalkylditin compounds received much attention for the generation of biaryls. In general, they have quite frequently been observed as by-products from the stannylation of aryl halides with ditin compounds. The intramolecular, optimized version is named Stille-Kelly reaction. ... 

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