16886-07-0Relevant academic research and scientific papers
Alkylation of the ambident indole ion in ionic liquids
Vavilina,Zicmanis,Drozdova,Mekss,Klavins
, p. 530 - 541 (2008)
Alkylation of the ambident indole anion in ionic liquids has been investigated. The reaction rate is greater in ionic liquids than in organic solvents. The polarity of certain ionic liquids has been determined to be located between methanol and acetonitrile. 2008 Springer Science+Business Media, Inc.
Iridium-catalyzed C-3 allylation of indoles with allylic alcohols promoted by a bronsted acid
Chen, Shu-Jie,Lu, Guo-Ping,Cai, Chun
supporting information, p. 1717 - 1724 (2014/07/08)
A highly regioselective method has been developed for the allylation of indoles with an iridium catalyst. This regioselective procedure uses allylic alcohols directly as allylating agents in the presence of a catalytic amount of sulfuric acid. A wide rang
C2-selective direct alkynylation of indoles
Tolnai, Gergely L.,Ganss, Stephanie,Brand, Jonathan P.,Waser, Jerome
supporting information, p. 112 - 115 (2013/03/28)
The first C2-selective alkynylation of indoles using the hypervalent iodine reagent triisopropylsilylethynyl-1,2-benziodoxol-3(1H)-one (TIPS-EBX) with Pd(II) as a catalyst is described. This convenient and robust method gives a single-step access to substituted alkynyl indoles with very high C2 selectivity. The reaction is orthogonal to classical Pd(0) cross-coupling reactions, as it is tolerant to bromide and iodide substituents. The used silyl protecting group can be easily removed to give terminal acetylenes.
Fast, efficient Ru(IV)-catalysed regioselective allylation of indoles using allyl alcohol (without additives) under mild conditions
Zaitsev, Alexey B.,Gruber, Stefan,Pregosin, Paul S.
, p. 4692 - 4693 (2008/10/09)
The new Ru(iv) salt, [Ru(η3-C3H 5)(Cp*)(CH3CN)2](PF6) 2, is an excellent catalyst for the regioselective allylation of a variety of indole compounds using allyl alcohol as substrate; there are no co-catalysts required in this chemistry and the yields and reaction conditions are very favorable. The Royal Society of Chemistry.
Regioselectivity Control in Alkylation Reactions of Indolyl Ambident Anion
Nunomoto, Sadaaki,Kawakami, Yuhsuke,Yamashita, Yuya,Takeuchi, Hisato,Eguchi, Shoji
, p. 111 - 114 (2007/10/02)
The regioselectivity of N- and C-3(β)-alkylations of indolylmetal salts was studied under various conditions.The effect of counter metal ion is crucial in determining the regioselectivity.In tetrahydrofuran, exclusive N-alkylation occurred with the potassium salt, but the extent of C-3-alkylation increased with the sodium and lithium salts and became predominant with the magnesium bromide salt.However, N-alkylation was favoured generally in more polar solvents and for alkyl toluene-p-sulphonates it was favoured even with magnesium bromide salts.The reactivity and regioselectivity of the alkylations were correlated with the calculated electron density of the indolyl anion and with 13C n.m.r. chemical shifts of the metal salts.
REACTIVITY OF UNSATURATED INDOLE DERIVATIVES TOWARDS ORGANOMETALLIC AND RADICAL POLYMERIZATION INITIATORS
Pini, Dario
, p. 473 - 478 (2007/10/02)
The ability of 3-allylindole (3-AIN) and 3-indolyl vinyl ketone (3-INVK) (prepared by literature methods) to polymerise has been investigated.After addition of pure 3-AIN to AlBu3i/TiCl3ARA catalyst, with molar ratios Al/Ti=3 and monomer/Ti=20, 3-AIN is recovered unchanged; on the contrary, if the monomer is previously complexed with an equimolar amount of either AlBu3i or TiCl3, the 3-(1-propyl)indole or a dimer are isolated, respectively.In every run no polymer formation was observed.In order to get information about interactions of the bimetallic Ziegler-Natta system with the indole nucleus, polymerisation of 4-methyl-1-pentene in the presence of the AlBu3i/TiCl3/indole system, using different values of indole/TiCl3 and indole/AlBu3i ratios, has also been carried out.Attempts to polymerise 3-INVK have been performed both by an anionic catalyst, such as ZnBu2i in tetrahydrofuran, and by a radical initiator, such as azobisisobutyronitrile in 2-propanol.In both cases no polymer was isolated, but when catalytic amounts of the initiators are employed, the monomer is recovered unchanged.When equimolar amounts of monomer to catalyst are used, 3-indolyl 4-methyl-1-pentyl ketone and 3-cyano-3-methyl-1-butyl 3-indolyl ketone are obtained in the anionic and radical polymerisation, respectively.Some hypotheses are put forward to explain the peculiar behaviour of vinyl monomers containing the indole nucleus.
