42951-53-1

Upstream product

• 111-86-4 n-Octylamine 
• 10271-57-5 1-chloro-2-(2-phenylethynyl)benzene 
• 615-41-8 2-iodochlorobenzene 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 21375-88-2 1-bromo-2-(phenylethenyl)benzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 111-83-1 1-bromo-octane 
• 120-72-9 indole 
• 42951-63-3 1-octyl-1H-indole 
• 591-50-4 iodobenzene 

Downstream Products

• 132426-87-0 1,1-bis(1-n-octyl-2-phenylindole-3-yl)ethylene 

Relevant academic research and scientific papers

Efficient synthesis of 2-substituted indoles based on palladium(II) acetate/tri-tert-butylphosphine-catalyzed alkynylation/amination of 1,2-dihalobenzenes

A simple, efficient palladium(II) acetate/tri-tert-butylphosphine-catalyzed indole synthesis from o-alkynylhalobenzenes, readily available from 1,2-dihalobenzenes, has been achieved in good to excellent yields. A one-pot, Pd(OAc)2/t-Bu3P-catalyzed sequential reaction from 1-chloro-2-iodobenzene, phenylacetylene and amines has also been achieved in good yields.

Utilizing Mor-DalPhos/palladium-catalyzed monoarylation in the multicomponent one-pot synthesis of indoles

The application of a Mor-DalPhos/palladium catalyst system in the one-pot, multicomponent assembly of substituted indoles from ortho-chlorohaloarenes, alkyl ketones (including acetone), and primary amines is reported. The described protocols offer improved substrate scope in all three reaction components, under more mild conditions and without the need for an additional drying agent. Also reported are the first examples of such multicomponent reactions where all reactants are combined at the start of the reaction, without the need for inert atmosphere reaction conditions.

Nickel-catalyzed, base-mediated amination/hydroamination reaction sequence for a modular synthesis of indoles

A catalytic system consisting of [Ni(cod)2] and ligand dppf enabled an efficient synthesis of differently substituted indoles through a modular reaction sequence, which consists of intermolecular aminations and intramolecular hydroaminations with ortho-alkynylhaloarenes.

General and efficient indole syntheses based on catalytic amination reactions

(Chemical Equation Presented) Highly flexible and efficient syntheses of the indole backbone are presented starting from o-alkynylhaloarenes. These transformations proceed via a palladium- or a copper-catalyzed amination reaction and a subsequent cyclization reaction in good to excellent yields. Furthermore, a multicatalytic one-pot indole synthesis starting from o-chloroiodobenzene is viable using a single catalyst consisting of an N-heterocyclic carbene palladium complex and Cul.

Three-component indole synthesis using ortho-dihaloarenes

A three-component synthesis of substituted indoles is accomplished starting from ortho-dihaloarenes through the use of a multicatalytic system consisting of an N-heterocyclic carbene palladium complex and CuI. The corresponding indole derivatives are obtained as single regioisomers in high yields of isolated product.

Direct palladium-catalyzed C-2 and C-3 arylation of indoles: A mechanistic rationale for regioselectivity

We have recently developed palladium-catalyzed methods for direct arylation of indoles (and other azoles) wherein high C-2 selectivity was observed for both free (NH)-indole and (NR)-indole. To provide a rationale for the observed selectivity ("nonelectrophilic" regioselectivity), mechanistic studies were conducted, using the phenylation of 1-methylindole as a model system. The reaction order was determined for iodobenzene (zero order), indole (first order), and the catalyst (first order). These kinetic studies, together with the Hammett plot, provided a strong support for the electrophilic palladation pathway. In addition, the kinetic isotope effect (KIEH/D) was determined for both C-2 and C-3 positions. A surprisingly large value of 1.6 was found for the C-3 position where the substitution does not occur (secondary KIE), while a smaller value of 1.2 was found at C-2 (apparent primary KIE). On the basis of these findings, a mechanistic interpretation is presented that features an electrophilic palladation of indole, accompanied by a 1,2-migration of an intermediate palladium species. This paradigm was used to design new catalytic conditions for the C-3 arylation of indole. In case of free (NH)-indole, regioselectivity of the arylation reaction (C-2 versus C-3) was achieved by the choice of magnesium base.