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• W2776459172 abstract "As C3 is the preferred site for electrophilic substitution, direct alkylation and acylation procedures are often effective. Even mild electrophiles such as alkenes with EW substituents can react at the 3-position of the indole ring. Techniques for preparation of 3-lithioindoles, usually by halogen-metal exchange, have been developed and this provides access not only to the lithium reagents but also to other organometallic reagents derived from them. The 3-position is also reactive toward electrophilic mercuration. The best procedures for 3-vinylation or 3-arylation of the indole ring involve palladium intermediates. Vinylations can be done by Heck reactions starting with 3-halo or 3-sulfonyloxyindoles. Under the standard conditions the active catalyst is a Pd(0) species which reacts with the indole by oxidative addition. A major consideration is the stability of the 3-halo or 3-sulfonyloxyindoles, and usually an EW substituent is required on nitrogen. Arylation reactions can involve generation of either a nucleophilic (for example, stannane, organozinc, boronic acid) or electrophilic (for example, halide or triflate) derivative of indole. A complementary reagent provides the 3-substituent and palladium is used to catalyze coupling. Coupling proceeds by oxidative addition of the electrophilic component on Pd(0) and ligand exchange with the nucleophilic component to generate a diarylpalladium(II) intermediate, which undergoes reductive elimination." @default.
• W2776459172 created "2018-01-05" @default.
• W2776459172 creator A5032729431 @default.
• W2776459172 date "1996-01-01" @default.
• W2776459172 modified "2023-09-23" @default.
• W2776459172 title "Introduction of Substituents at C3" @default.
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• W2776459172 doi "https://doi.org/10.1016/b978-012676945-6/50031-4" @default.
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