- Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation
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Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.
- Basak, Shubhajit,Paul, Tripti,Punniyamurthy, Tharmalingam
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supporting information
p. 554 - 558
(2022/01/20)
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- Synthesis of trifluoromethylindolocarbazoles, novel cyclic 18-membered and 27-membered N-arylmethyldi- and triindoles and an N-arylmethyltetraindolyltrimethane
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5,11-Dihydro-5,11-diarylmethyl-6-trifluoromethylindolo[3,2-b]carbazoles (3b-d) have been synthesised from both N-arylmethylindole-3-carbinols (1b-d) and N,N′-diarylmethyl-3,3′-diindolylmethanes (2b, c and f) by treatment with trifluoroacetic anhydride. The cyclic N-arylmethylindoledi- and trimers (4c-f) and the 3-trifluoroacetylindoles (5a and b) have also been obtained from this reaction. Thermal reaction of 1b-d furnishes 2b, c and f, but 1c also affords the N-arylmethyltriindolyldimethane (2d) and the N-arylmethyltetraindolyltrimethane (2e). The results are discussed and the plausible reaction mechanism is very briefly presented.
- Biswas,Saha, Aparna,Mallik, Haimanti
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p. 601 - 606
(2007/10/03)
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- Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane
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5,11-Dihydro-5,11-dibenzyl-6-trifluoromethylindolo[3,2-b]carbazole (6) and the cyclic N-benzylindole trimer 4 were synthesized from both N-benzylindole-3-methanol (1) and N,N'-dibenzyl-3,3'-diindolylmethane (2) by treatment with trifluoroacetic anhydride. The former also gave the 36-membered cyclic N-benzylindole tetramer 7, and the latter furnished N-benzyl-3-trifluoroacetylindole (8). Heating 1 in aqueous methanol also yielded the trimer 4 along with 2, the N-benzylitriindolyldimethane 3, and the N-benzyltetraindolyltrimethane 5 whose structure and solid-state conformation were determined by X-ray crystallographic analysis. The results are discussed and plausible mechanisms of the reactions leading to 3-8 are presented.
- Biswas, Kshetra M.,Mallik, Haimanti,Saha, Aparna,Halder, Sumita,McPhail, Andrew T.
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p. 1227 - 1239
(2007/10/03)
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