5192-14-3

Upstream product

• 5457-31-8 (3-indolylmethyl)trimethylammonium iodide 
• 6921-34-2 benzylmagnesium chloride 
• 120-72-9 indole 
• 60-12-8 2-phenylethanol 
• 18328-11-5 3-benzyl propionaldehyde 
• 100-63-0 phenylhydrazine 
• 40281-54-7 1-(1H-indol-3-yl)-2-phenylethan-1-one 
• 496-15-1 1-indoline 
• 15121-84-3 2-nitro-benzeneethanol 

Downstream Products

• 1449683-67-3 methyl 2-(3-phenethyl-1H-indol-2-yl)acetate 

Relevant academic research and scientific papers

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex

A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles can be obtained in high yields. Experimental studies indicate a metal-ligand cooperative catalysis mechanism.

Manganese-Catalyzed Regioselective Dehydrogenative C-versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation

The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air-and moisture-stable manganese catalyst provides access to either C3-or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.

Divergent dehydrogenative coupling of indolines with alcohols

The dehydrogenative coupling of indolines with alcohols catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcohols and catalyzes the coupling reactions. Mechanistic studies reveal that a borrowing hydrogen-dehydrogenation process and a dehydrogenationborrowing hydrogen process are involved in N-alkylation and C3-alkylation reactions, respectively. The C3-alkylation reaction involves the direct coupling of two sp3 carbon centers.

Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3

We report the FeCl3-mediated direct addition of electron-rich arenes to the C2-position of electrophilic N-Ac indoles under mild conditions (room temperature, air). No functional group is required on the arene nucleophile: one of its C-H bonds is added to the C2=C3 double bond of the indole nucleus in a Friedel-Crafts-type reaction. This dearomatisation process delivered a broad range of C2-arylated indolines.

Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction

A conjugate addition/asymmetric protonation/aza-Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl4 and 3,3′-dibromo-BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6-dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl4BINOL complex serves as a chiral Lewis-acid-assisted Br?nsted acid.

General and selective C-3 alkylation of indoles with primary alcohols by a reusable Pt nanocluster catalyst

The platinum rule: Heterogeneous, additive-free C-3 selective alkylation of indoles by aliphatic and aromatic alcohols proceeded under transfer hydrogenation conditions with the reusable Pt/θ-Al2O 3 catalyst (see scheme; TON=turnover number). Copyright

Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols

The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3) 3/DPEphos {DPEphos = bis[(2-diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3-benzylindole. The corresponding 3-benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl 2(PPh3)3/DPEphos in the presence of K 3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3-alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst-mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation. Copyright