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The coupling of an acetylide and tertiary alkyl halide is an example of a reaction that cannot be accomplished with alkali metal acetylides, which displace halides in an S N 2 fashion. The corresponding alkynylalanes are able to couple to tertiary halides via an S N 1-like mechanism. [4] (11)
The scope of the Corey-House synthesis is exceptionally broad, and a range of lithium diorganylcuprates (R 2 CuLi, R = 1°, 2°, or 3° alkyl, aryl, or alkenyl) and organyl (pseudo)halides (RX, R = methyl, benzylic, allylic, 1°, or cyclic 2° alkyl, aryl, or alkenyl and X = Br, I, OTs, or OTf; X = Cl is marginal) will undergo coupling as the nucleophilic and electrophilic coupling partners ...
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]
Traditionally, the alkylating agents are alkyl halides. Many alkylating agents can be used instead of alkyl halides. For example, enones and epoxides can be used in presence of protons. The reaction typically employs a strong Lewis acid, such as aluminium chloride as catalyst, to increase the electrophilicity of the alkylating agent. [6]
The Wurtz–Fittig reaction is the chemical reaction of an aryl halide, alkyl halides, and sodium metal to give substituted aromatic compounds. [1] Following the work of Charles Adolphe Wurtz on the sodium-induced coupling of alkyl halides (the Wurtz reaction), Wilhelm Rudolph Fittig extended the approach to the coupling of an alkyl halide with an aryl halide.
The synthesis of (E)-4-iodo-3-methylbut-3-en-1-ol [12] shown below is a typical application of this reaction: For terminal alkynes, the reaction generally proceeds with good regioselectivity (>90:10 rr) and complete syn selectivity, even in the presence of propargylic or homopropargylic heteroatom substituents.
Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen (F, Cl, Br, I). Haloalkanes have been known for centuries. Chloroethane was produced in the 15th century. The systematic synthesis of such compounds developed in the 19th century in step with the ...
The reaction also applies to acyl halides as electrophiles, which results in the formation of 1,3-diketones (Stork acylation). [2] It is also effective for activated sp 3 alkyl electrophiles, including benzylic, allylic/propargylic, α-carbonyl (e.g., bromoacetone), and α-alkoxy (e.g., methoxymethyl chloride) alkyl halides.