53541-90-5

Upstream product

• 120-72-9 indole 
• 589-18-4 4-Methylbenzyl alcohol 
• 944686-02-6 (1H-indol-3-yl)(p-tolyl)methanol 
• 487-89-8 Indole-3-carboxaldehyde 
• 89980-67-6 p-methylbenzylmagnesium bromide 
• 104-82-5 4-Methylbenzyl chloride 
• 5339-85-5 2-aminophenethyl alcohol 
• 15121-84-3 2-nitro-benzeneethanol 
• 496-15-1 1-indoline 
• 459-56-3 4-fluorobenzylic alcohol 
• 104-81-4 4-Methylbenzyl bromide 

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.).

Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.

Sulfonimide photo-acid generator with high acid yield

The invention discloses a sulfonimide photo-acid generator with high acid yield. The sulfonimide photo-acid generator has a structure as shown in a general formula (A) in the description. The acid generator has high sensitivity to active energy rays with the wavelength of 300-450nm, particularly 365nm (I rays) and 405nm (H rays), and is good in solubility and strong in acidity.

Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method

An inexpensive, air-stable, isolable nickel catalyst is reported that can perform chemoselective C3-alkylation of indoles with a variety of alcohols following "borrowing hydrogen". A one-pot, cascade C3-alkylation starting from 2-aminophenyl ethyl alcohols, and thus obviating the need for pre-synthesized indoles, further adds to the broad scope of this method. The reaction is radical-mediated, and is significantly different from other examples, often dictated by metal-ligand bifunctionality. This journal is

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.

Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen

We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and H2O that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis of the preliminary experimental observations, we propose that the reaction proceeds through a borrowing hydrogen process.

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.

A highly efficient route to C-3 alkyl-substituted indoles via a metal-free transfer hydrogenation

A highly efficient route to C-3 alkyl-substituted indoles via completely metal-free catalytic transfer hydrogenation of 3-indolemethanols was developed. This process proceeds via vinylogous iminium intermediates formed in situ in the presence of Br?nsted

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

Environmentally friendly and regioselective C3-alkylation of indoles with alcohols through a hydrogen autotransfer strategy

The direct alkylation of indoles using KOH and alcohols, as initial source of the electrophile, under solvent-free conditions is a safe and environmentally benign strategy for selective modification of these structures at the C 3-position, without using hazardous and difficult to handle bromide or iodide derivatives or toxic and expensive transition metal catalysts. The protocol shows a broad scope, including halogenated indoles and secondary alcohols.