96005-17-3

Upstream product

• 603-76-9 1-methylindole 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 2216-94-6 phenylpropynoic acid ethyl ester 

Relevant academic research and scientific papers

Diastereoselective Synthesis of Tetrahydrospiro[carbazole-1,3′-indolines] via an InBr3-Catalyzed Domino Diels-Alder Reaction

A simple InBr3-catalyzed domino reaction of indoles, phenylacetylenes, and various 3-methyleneoxindolines in toluene is described. This reaction not only provided a convenient synthetic protocol for polysubstituted tetrahydrospiro[carbazole-1,3′-indolines] in good yields but also gave completely different diastereoisomers of the tetrahydrospiro[carbazole-1,3′-indolines] to that of the previously reported TfOH-catalyzed one-pot reaction of indoles, acetophenones, and 3-methyleneoxindolines. Additionally, the InBr3-catalyzed reaction of the initially prepared 1,1′-bis(indolyl)phenylethanes with 3-phenacylideneoxindolines also gave the corresponding tetrahydrospiro[carbazole-1,3′-indolines] in good yields and with excellent diastereoselectivity. The reaction mechanism involved the sequential in situ generation of reactive dienophilic 3-alkenylindole, the Diels-Alder reaction, and the Lewis acid controlled diastereoisomerization process.

Selectivity control in gold-catalyzed hydroarylation of alkynes with indoles: Application to unsymmetrical bis(indolyl)methanes

Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-c

Lewis acid-catalyzed double addition of indoles to ketones: Synthesis of bis(indolyl)methanes with all-carbon quaternary centers

We report herein a Lewis acid-catalyzed nucleophilic double-addition of indoles to ketones under mild conditions. This process occurs with various ketones ranging from dialkyl ketones to diaryl ketones, thereby providing access to an array of bis(indolyl)

Gold(I) Complexes in Ionic Liquids: An Efficient Catalytic System for the C-H Functionalization of Arenes and Heteroarenes under Mild Conditions

Use of ionic liquids bearing the proper counteranion as reaction solvents allows to boost the reactivity of gold(I) complexes as catalysts in the hydroarylation of alkynes with arenes and heteroarenes. Several commercial complexes of general structure LAu

B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes: An approach toward bis(indolyl)alkanes

The first example of the metal-and solvent-free B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes was disclosed. Both N-H and N-protected indoles were tolerated, leading to a wide spectrum of versatile bis

Easy access to a library of alkylindoles: Reductive alkylation of indoles with carbonyl compounds and hydrosilanes under indium catalysis

By applying carbonyl compounds as sources of alkyl groups to the indium-catalyzed reductive alkylation of indoles, a reliable and practical method capable of offering a wide range of alkylindoles with structural diversity has been developed. An important

Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions

An efficient indole-to-carbazole strategy has been developed under metal-free conditions. This carbazole formation was highly promoted by NH4I with high regioselectivity through formal [2 + 2 + 2] annulation of indoles, ketones, and nitroolefins. It thus conveniently enabled the assembly of a large number of diversified carbazole products with good tolerance of a broad range of functional groups.

Platinum(II) complexes with novel diisocyanide ligands: Catalysts in alkyne hydroarylation

A series of novel diisocyanide ligands (o-CNC6H 4O)2Y (diNC-1: Y = P(O)Ph; diNC-2: Y = o-C(O)C 6H4C(O); diNC-3: Y = m-C(O)C6H4C(O); diNC-4: Y = C(O)C2H4C(O); diNC-5: Y = trans-C(O)C 2H2C(O)) was successfully synthesized by reaction of lithium 2-isocyanophenate (generated in situ from benzoxazole and n-BuLi) and a diacylic or phosphonic dichloride. The corresponding platinum(II) complexes of general formula [PtX2(diNC)]1,2 (X = Cl, Me; diNC = diisocyanide ligand) were isolated by simple substitution of 1,5-cyclooctadiene in the starting [PtX2(COD)] complexes. The structure of the complexes, mononuclear or dinuclear, was confirmed by single-crystal X-ray analysis. A dinuclear complex of formula {(μ-diNC)[cis-PtCl 2(PPh3)]2} could also be obtained with the diisocyanide ligand having a rigid fumaryl bridge and consequently the isocyanide moieties pointing in opposite directions. All the complexes were employed as catalysts in the hydroarylation of alkynes, showing generally good activity and selectivity toward the trans-hydroarylation product. With N-methylindole as aromatic substrate the major product was instead a heterocycle:alkyne 2:1 adduct.

An efficient one pot conversion of alkynes to bis(indolyl) and bis(pyrrolyl)alkanes in aqueous ethanol

Mercury (II) chloride efficiently catalyzes the reaction between indoles /pyrrole and substituted phenyl acetylenes to furnish bis(indolyl)alkane and bis(pyrrolyl)alkane in good to excellent yields under room temperature and moderate reaction time. The re

Rhenium-catalyzed regiodivergent addition of indoles to terminal alkynes

An efficient rhenium-catalyzed site-switchable addition of indoles to terminal alkynes is described. A variety of bisindolylalkane derivatives are expeditiously synthesized in high yields with excellent regioselectivity. Preliminary mechanistic study shed