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The Stille reaction is a chemical reaction widely used in organic synthesis.The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes).
John Kenneth Stille (May 8, 1930 – July 19, 1989) was an American chemist who discovered the Stille reaction. He received B.A. and M.A. degrees from the University of Arizona before serving in the Navy during the Korean War. He received his Ph.D. from the University of Illinois, where he studied under Carl Shipp Marvel. [1]
The increased reactivity relative to other cross-coupling reactions makes the Negishi coupling ideal for joining complex intermediates in the synthesis of natural products. [8] Additionally, Zn is more environmentally friendly than other metals such as Sn used in the Stille coupling. The Negishi coupling historically is not used as much as the ...
One was limited to the production of N-protected 2-stannylindoles through metalation by a process known as Stille coupling. [6] The N-unprotected 2-stannylindoles generated from the Fukuyama Synthesis can be readily oxidized with iodine opening up an area of chemistry that allows for the synthesis of a variety compounds utilizing the 2 ...
A stereoretentive Stille coupling using alkyl carbastannatranes. Palladium also catalyzes Stille coupling of secondary alkyl carbastannatranes and aryl electrophiles. [ 12 ] [ 13 ] This report serves as the first example of employing chiral alkyl carbastannatrane reagents in enantioselective synthesis .
Often, however, cross-coupling refers to a metal-catalyzed reaction of a nucleophilic partner with an electrophilic partner. Mechanism proposed for Kumada coupling (L = Ligand , Ar = Aryl ). In such cases, the mechanism generally involves reductive elimination of R-R' from L n MR(R') (L = spectator ligand ).
The Liebeskind–Srogl coupling reaction is an organic reaction forming a new carbon–carbon bond from a thioester and a boronic acid using a metal catalyst. It is a cross-coupling reaction . [ 1 ] This reaction was invented by and named after Jiri Srogl from the Academy of Sciences, Czech Republic, and Lanny S. Liebeskind from Emory ...
Vinyl iodides are versatile molecules that serve as important building blocks and precursors in organic synthesis. They are commonly used in carbon-carbon forming reactions in transition-metal catalyzed cross-coupling reactions, such as Stille reaction, Heck reaction, Sonogashira coupling, and Suzuki coupling. [1]