Polymerisation of indole. Part 3. Two indolylquinolines, an indole tetramer, and the dihydro derivative of the indole dimer

Synthesis of a Trifluoromethylindolocarbazole, Novel Cyclic 27- and 36-Membered N-Benzyltri- and -tetraindoles, and an N-Benzyltetraindolyltrimethane

“…Non-hydrogen atom fractional coordinates and equivalent isotropic thermal parameters for 5 (esd values in parentheses) (3) 6.42 (7) C(11) 0.1813 (3) 0.5528 (2) 0.0965 (4) 8.42(9) C (12) 0.2362 (3) 0.5638 (2) 0.0127 (3) 7.46(9) C (13) 0.3244 (3) 0.5251 (2) À0.0063 (3) 5.85 (7) C(14) 0.3586 (2) 0.4741 (1) 0.0588 (2) 4.76 (6) (2) 3.59 (5) The protons and the carbon atom of one N±CH 2 of 6 were shifted down®eld in its 1 H and 13 C NMR spectra relative to those of the other N±CH 2 moiety, presumably because the protons and the carbon of one N±CH 2 bear six-bond and ®ve-bond relationships [18,19], respectively, with the¯uorine atoms of its CF 3 group, whereas there exists no such relationship with those of the other N±CH 2 group. This observation led us to propose structure 6.…”

Regio‐ and Stereoselective Allylation and Crotylation of Indoles at C2 Through the Use of Potassium Organotrifluoroborate Salts

“…We considered that the intermediacy of an in situ generated allyldifluoroborane species might similarly allow the addition to indoles via their 3H-indole tautomers. Initial reaction optimizations were carried out using potassium allyltrifluoroborate 1 a and indole 2 a. Activation by K10 led to only moderate yields of indoline 3 a because of competing side reactions of 2 a, while the use of an indium-based protocol, which had been successfully developed for additions to ketones, [13g] did not give the desired product 3 a ( [14] ) at higher concentrations, while conversion was poor at lower concentrations. Catalytic Yb(OTf) 3 was also capable of promoting addition of 1 a to 2 a (Table 1, entry 4).…”

Synthesis of Indolo[3,2‐b]carbazoles via an Anomeric‐Based Oxidation Process: A Combined Experimental and Computational Strategy

“…Among of five likely isomers, 5,11‐dihydroindolo[3,2‐ b ]carbazole (referred to herein as indolo[3,2‐ b ]carbazole or ICZ) has shown attractive structural and electrical properties (high charge carrier mobility) combined with good stability under atmospheric changes that makes them good components for use in organic electronics . Numerous synthetic procedures for the synthesis of symmetrical and unsymmetrical indolo[3,2‐ b ]carbazoles have been reported in the literature, most of which depend on multi‐step sequences characterized by low overall yield . A comprehensive overview of the synthesis and characterization of indolo[3,2‐ b ]carbazoles can be found in the literature .…”