- Decarboxylative halogenation of indolecarboxylic acids using hypervalent iodine(III) reagent and its application to the synthesis of polybromoindoles
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Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-brom
- Hamamoto, Hiromi,Umemoto, Hideaki,Umemoto, Misako,Ohta, Chiaki,Fujita, Emi,Nakamura, Akira,Maegawa, Tomohiro,Miki, Yasuyoshi
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p. 561 - 572
(2015/05/20)
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- Hypervalent iodine(III) mediated decarboxylative halogenation of indolecarboxylic acids for the synthesis of haloindole derivatives
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The treatment of 1-methylindole-2,3-dicarboxylic acid with hypervalent iodine(III) reagent, phenyliodine diacetate (PIDA), in the presence of lithium bromide gave 1-methyl-3,3-dibromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and 2,3-diiodo-indole derivatives were obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. Georg Thieme Verlag Stuttgart New York.
- Hamamoto, Hiromi,Umemoto, Hideaki,Umemoto, Misako,Ohta, Chiaki,Dohshita, Masashi,Miki, Yasuyoshi
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scheme or table
p. 2593 - 2596
(2010/11/24)
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- Decarboxylative bromination of indole-2,3-dicarboxylic acids using oxone or can in the presence of lithium bromide
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The treatment of l-methylindole-2,3-dicarboxylic acid with Oxone and lithium bromide produced 3,3-dibromo-l-methyloxindole. However, the reaction of 1-benzenesulfonylindole-2,3-dicarboxylic acid with Oxone and lithium bromide afforded l-benzenesulfonyl-2,
- Umemoto, Hideaki,Umemoto, Misako,Ohta, Chiaki,Dohshita, Masashi,Tanaka, Hiroki,Hattori, Syo,Hamamoto, Hiromi,Miki, Yasuyoshi
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scheme or table
p. 2845 - 2850
(2010/04/29)
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- A simple catalytic synthesis of condensed pyridones from o-bromoarylcarboxamides involving ipso substitution via palladacycles
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A catalytic synthesis of condensed pyridones starting from o-bromoaromatic carboxamides is reported using Pd(OAc)2/TFP as catalyst, K2CO3 as a base in DMF at 105 °C. Under these conditions an unprecedented reaction sequenc
- Ferraccioli, Raffaella,Carenzi, Davide,Motti, Elena,Catellani, Marta
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p. 722 - 723
(2007/10/03)
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- Selective lithiation of 2,3-dibromo-1-methylindole. A synthesis of 2,3-disubstituted indoles
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Indole (1) can be converted to 2,3-dibromo-1-methylindole (3) in two operations (92% yield). Treatment of 3 with tert-butyllithium effects clean monolithiation to 3-bromo-2-lithio-1-methylindole (4), which can be trapped with various electrophiles to afford the 3-bromo-2-substituted indoles (5-8) in 85-99% yield. A second bromine-lithium exchange reaction and quenching with electrophiles yields the 2,3-disubstituted indoles (9-10) in 88-95% yield.
- Liu, Yanbing,Gribble, Gordon W
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p. 7135 - 7137
(2007/10/03)
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