72228-54-7

Upstream product

• 19012-03-4 N-methyl-3-formylindole 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 603-76-9 1-methylindole 
• 5153-67-3 nitrostyrene 
• 50901-75-2 2-phenyl-vinyloxirane 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 100-42-5 styrene 
• 3112-88-7 Benzyl phenyl sulfone 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 81471-20-7 3-bromo-1-methyl-1H-indole 
• 1074-12-0 phenylglyoxal hydrate 
• 1373435-98-3 C₂₄H₂₁NO₃S 

Downstream Products

• 72228-49-0 β-(N-Methyl-2-methyl-3-indolyl)styrene 
• 72228-52-5 9,9a-Dimethyl-3-phenyl-9,9a-dihydro-3H-[1,2]dioxino[3,4-b]indole 

Relevant academic research and scientific papers

Visible-Light-Enabled Aerobic Denitrative C3-Alkenylation of Indoles with β-Nitrostyrenes

Herein, we unveil the first visible-light-mediated alkenylation reaction of indoles. The reaction follows a denitrative radical pathway where β-nitrostyrenes have been utilized as the alkene precursors for the C3-styrenylation of indoles under visible-light irradiation to afford biologically and synthetically important 3-alkenylindoles. High regioselectivity, absence of any photocatalyst, metal, external oxidant, acid or base, and the use of visible light and air as inexpensive clean reagents are the key highlights of the developed method.

Syntheses of diarylethenes by perylene-catalyzed photodesulfonylation from ethenyl sulfones

Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.

Chiral Imidodiphosphoric Acid-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Poly-Substituted 3,4-Dihydro-2 H-pyrans: [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketoesters and 3-Vinylindoles

Imidodiphosphoric acids were employed to catalyze inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters and 3-vinylindoles. A series of optically active 3,4-dihydro-2H-pyran derivatives with three contiguous stereogenic centers was synthesized in excellent yields (70-99%), diastereoselectivities (>20:1), and enantioselectivities (73-99%). The resulting indole containing 3,4-dihydro-2H-pyran could be converted to tetrahydropyran derivatives, which appear in several biological active compounds by simple hydrogenation reduction.

Pd(II) supramolecular cage-catalyzed successive oxidative coupling: One-pot and regioselective synthesis of functionalized carbazoles from indoles

Carbazole is an important compound in pharmaceuticals and functional materials. A new Pd(II) supramolecular cage-catalyzed protocol for the synthesis of multifunctional carbazoles from indoles is described through regioselective successive oxidative Heck reactions. This new protocol is highly efficient, with a low Pd (2.4 mol%) catalyst loading and good compatibility for both N-H free and N-protected indole substrates. Moreover, it can be used to synthesize carbazoles with various functional groups by a one-pot two-step procedure. The excellent catalytic activity can be attributed to the distinct properties of the supramolecular cage structure in uniformly distributive and well-defined Pd(II) active centers on the cage surfaces.

Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[ c]furans

A highly enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3 + 2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with 3-stylindoles was achieved by using Ming-Phos as a chiral ligand. A variety of chiral highly substituted cyclopenta[c]

Solvent-controlled highly regio-selective thieno[2,3-: B] indole formation under metal-free conditions

An efficient three-component thieno[2,3-b]indole formation method was developed under metal-free conditions. The cascade cyclization was enabled by acid-promoted annulation of indoles, ketones and sulfur powder, which enabled modular synthesis of 2-substituted and 3-substituted thieno[2,3-b]indoles with excellent regioselectivity and broad functional group tolerance. DMF solvent played an important role in the regioselectivity control.

Three-Component Thieno[2,3-b]indole Synthesis from Indoles, Alkenes or Alkynes and Sulfur Powder under Metal-Free Conditions

A Bronsted acid promoted three-component synthesis of substituted thieno[2,3-b]indole has been developed starting from indoles, alkenes or alkynes, and sulfur powder. N,N-Dimethylformamide plays an important role to convert the starting materials into the fused products. Various functional groups attached to substrates were well tolerated to afford the corresponding products in moderate to good yields under very simple reaction conditions. (Figure presented.).

In site preparation of Pd(II)-MoS2 complex: A new high-efficiency catalyst for alkenylation of heteroaromatics by direct C-H bond activation

Pd(II)-MoS2 catalyst was designed by affording Pd2+ salt on the surface of single-layered molybdenum disulfide nanosheets.. Based on the dispersible template, this metal salt and molybdenum disulfide complex offered several advantages, including easy preparation, low cost, and capability to prepare excellent dispersible metal ion cluster nanostructures. The application of this complex in alkenylation of heteroaromatics was reported. Direct C-H activation of indoles, furans and thiophenes was carried out to combine with several kinds of terminal olefins. This catalyst also performed high efficiency in several other kinds of coupling reactions. Thus, a universal suitable catalyst for C-H activation and CC bond formation was invented by a convenient in situ preparation.

General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand

A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.

Aerobic dehydrogenative Heck reactions of heterocycles with styrenes: A negative effect of metallic Co-oxidants

The aerobic dehydrogenative Heck reaction (DHR) of heterocycles with styrenes was found to be more efficient in the absence of metallic cooxidants. According to a study of the isotope effect, the C-H cleavage was the rate-determining step of the catalytic