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.[1] The Hiyama coupling has been applied to the synthesis of various natural products.[2]
: aryl, alkenyl or alkynyl
: aryl, alkenyl, alkynyl or alkyl
: Cl, F or alkyl
: Cl, Br, I or OTf
^Hatanaka, Y.; Hiyama, T. (1988). "Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate". Journal of Organic Chemistry. 53 (4): 918–920. doi:10.1021/jo00239a056.
^Denmark, S. E.; Regens, C. S. (2008). "Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods". Accounts of Chemical Research. 41 (11): 1486–1499. doi:10.1021/ar800037p. PMC 2648401. PMID 18681465.
The Hiyamacoupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon...
District, Hokkaidō, a district in Hiyama Subprefecture Hiyamacoupling, a carbon-carbon bond-forming reaction Nozaki–Hiyama–Kishi reaction, a carbon-carbon...
for his work in developing the Nozaki-Hiyama-Kishi reaction and the Hiyamacoupling. He is currently a professor at the Chuo University Research and Development...
cross-coupling methods. Despite the subsequent development of alternative reactions (Suzuki, Sonogashira, Stille, Hiyama, Negishi), the Kumada coupling continues...
often replaced by palladium coupling reactions such as the Heck reaction, the Hiyamacoupling, and the Sonogashira coupling. Biphenylenes had been obtained...
In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid...
pentaorganosilicate: The stability of hypervalent silicon is the basis of the Hiyamacoupling, a coupling reaction used in certain specialized organic synthetic applications...
the cross-coupling of organo-halides and organolithium reagents, ruthenium catalysts have also been demonstrated. Heck reaction Hiyamacoupling Suzuki reaction...
reactions include organostannane additions, Barbier reactions, and the Nozaki–Hiyama–Kishi reaction. In the aldol reaction, the metal enolates of ketones, esters...
which is prepared by direct bromination of the diphenol. Shimizu, Masaki; Hiyama, Tamejiro (2005). "Modern Synthetic Methods for Fluorine-Substituted Target...
zinc which can then do an addition into the aldehyde substituent. Nozaki–Hiyama–Kishi reaction Indium mediated allylation Barbier reaction @ University...
use of preformed allylmetal reagents. Catalytic variants of the Nozaki-Hiyama-Kishi reaction represent an alternative method for asymmetric carbonyl allylation...
Global Information![{\displaystyle {\begin{matrix}{}\\{\ce {{R-SiR''_{3}}+R'-X->[\mathrm {F^{-}} ][{\text{Pd cat.}}]R-R'}}\end{matrix}}}](https://wikimedia.org/api/rest_v1/media/math/render/svg/45686837800f1a0e625c8ab13b8224dd6e26a10e "The General Scheme for the Hiyama Coupling")
