Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: nitrogen-directed aromatic borylation.
نویسندگان
چکیده
Ir-catalyzed borylation of 2-substituted indoles selectively yields 7-borylated products in good yields. N-Protection, required for previous functionalizations of 2-substituted indoles, is unnecessary.
منابع مشابه
One-pot borylation/amination reactions: syntheses of arylamine boronate esters from halogenated arenes.
[reaction: see text] A one-pot protocol for converting 1,3- and 1,4-substituted aryl halides to arylamine boronate esters is described. This is achieved by sequential Ir-catalyzed aromatic borylation at the least hindered C-H bond of the aryl halide and subsequent Pd-catalyzed C-N coupling at the halide position of the crude arylboronic ester.
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[reaction: see text] 5-Substituted 3-amidophenols are prepared by subjecting 3-substituted halobenzenes to an Ir-catalyzed aromatic borylation, followed by a Pd-catalyzed amidation, and finally an oxidation of the boronic ester intermediate. The entire C-H activation borylation/amidation/oxidation sequence can be accomplished without isolation of any intermediate arenes. Usefully, amide partner...
متن کاملNickel-catalyzed borylation of arenes and indoles via C-H bond cleavage.
The first nickel-catalyzed method for the borylation of carbon-hydrogen bonds in arenes and indoles is described. The use of an N-heterocyclic carbene ligand is essential for an efficient reaction, with an N-cyclohexyl-substituted derivative being optimal. This method is readily applied to the gram scale synthesis of 2-borylindole.
متن کاملBoc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles.
Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions beta to N. The Boc group can be removed on thermolysis or left intact during subsequent transformations.
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ورودعنوان ژورنال:
- Journal of the American Chemical Society
دوره 128 49 شماره
صفحات -
تاریخ انتشار 2006