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The mechanism of the Stille reaction has been extensively studied. [11] [23] The catalytic cycle involves an oxidative addition of a halide or pseudohalide (2) to a palladium catalyst (1), transmetalation of 3 with an organotin reagent (4), and reductive elimination of 5 to yield the coupled product (7) and the regenerated palladium catalyst (1).
The Stille reaction has been used to make an antitumor agent, (±)-epi-jatrophone; [3] the Suzuki reaction has been used to make an antitumor agent, oximidine II; [4] the Sonogashira reaction has been used to make an anticancer drug, eniluracil; [5] and the Negishi reaction has been used to make the carotenoid β-carotene via a transmetalation ...
In the Stille reaction, sp 2-hybridized organic halides (e.g. vinyl chloride CH 2 =CHCl) catalyzed by palladium: R 1 −X + R 2 −Sn(R 3 ) 3 Pd catalyst ———→ R 1 −R 2 + X−Sn(R 3 ) 3 Organotin compounds are also used extensively in radical chemistry (e.g. radical cyclizations , Barton–McCombie deoxygenation , Barton ...
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]
Often cross-coupling reactions require metal catalysts. One important reaction type is this: R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryl; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds.
Gustav Stille (1845–1920), physician and writer; Hans Stille (1876–1966), German geologist; John Kenneth Stille (1930–1989), American chemist, originator of the Stille reaction; Mary Ingram Stille (1854-1935), American historian, journalist, and temperance reformer; Max Stille (1853–1906), Swedish ínstrument maker and entrepreneur
The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). ). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity
The Cadiot–Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper(I) salt such as copper(I) bromide and an amine base. [ 1 ] [ 2 ] The reaction product is a 1,3-diyne or di- alkyne .