Search results
Results from the WOW.Com Content Network
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).
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]
Such reactions are widely practiced for the synthesis of fine chemicals. Prominent coupling reactions include the Heck , Suzuki , Sonogashira coupling , Stille reactions , and the Kumada coupling .
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 ...
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.
The key steps of the synthesis of the rearrangement substrate leading to the starting materials necessary for the aza-Cope/Mannich reaction included a Stille reaction to piece together two precursors, an epoxidation of a double bond using tert-Butyl hydroperoxide, a Wittig reaction to convert the ketone to an alkene, and a cyclization step ...
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