137449-26-4

Upstream product

• 13228-39-2 1-ethyl-2-phenyl-1H-indole 
• 74-85-1 ethene 
• 622-76-4 1-phenyl-1-butyne 
• 826-42-6 N,N-diethylaniline N-oxide 
• 612-64-6 N-ethyl-N-nitrosoaniline 
• 99290-14-9 1-(3-ethyl-2-phenyl-1H-indol-1-yl)ethan-1-one 

Relevant academic research and scientific papers

Platinum(II)-catalyzed intermolecular hydroarylation of unactivated alkenes with indoles

Ethylene, α-olefins, and vinyl arenes undergo platinum-catalyzed hydroarylation with substituted indoles in moderate to good yield. The Royal Society of Chemistry 2006.

Rhodium-catalyzed annulation of tertiary aniline N-oxides to N-alkylindoles: Regioselective C-H activation, oxygen-atom transfer, and N-dealkylative cyclization

[Cp?RhIII]-catalyzed annulation of tertiary aniline N-oxides with alkynes was reported to achieve the challenging ortho C-H functionalization of tertiary anilines via N-O bond acting as a traceless directing group. More significantly, this system represents the first example which integrates C-H activation, oxygen-atom transfer, and N-dealkylative cyclization in one reaction. This unprecedented coupling reaction has allowed the construction of N-alkylindole derivatives in high efficiency with broad substrate scope and good functional group tolerance.

Rhodium(III)-catalyzed indole synthesis using N-N bond as an internal oxidant

We report herein a Rh(III)-catalyzed cyclization of N-nitrosoanilines with alkynes for streamlined synthesis of indoles. The synthetic protocol features a distinct internal oxidant, N-N bond, as a reactive handle for catalyst turnover, as well as a hitherto tantalizingly elusive intermolecular redox-neutral manifold, predicated upon C-H activation, for the formation of a five-membered azaheterocycle. The compatibility of seemingly dichotomous acidic and basic conditions ensures reaction versatility for multifarious synthetic contexts. The tolerance of an array of auxiliary functional groups potentially permits predefined, programmable substitution patterns to be incorporated into the indole scaffold. Comprehensive mechanistic studies, under acidic condition, support [RhCp*]2+ as generally the catalyst resting state (switchable to [RhCp*(OOCtBu)]+ under certain circumstance) and C-H activation as the turnover-limiting step. Given the variety of covalent linkages available for the nitroso group, this labile functionality is likely to be harnessed as a generic handle for strikingly diverse coupling reactions.

Diborane as reducing agent: Part VII - Novel reduction of indole-1-ketones to 1-alylindoles to 1-alkylindoles and mechanism of reduction of indole-1-aldehydes and ketones

Borane/THF reduction of nine indole-1-ketones (1a-1i) forms 1-ethylindoles (6a-6h) and the 1-benzylindole (6i) in 50-80percent yields.The ketones 1h and 1i, each of which bears phenyl groups at positions 2 and 3, also undergo deacylation to furnish 2,3-diphenylindole (8) in ca. 40percent yield.The mechanism of formation of both 8 and 6a-6i have been rationalised.The rate of borane/THF reduction of 1 is apparently slower than that of indole-1-carboxaldehydes (9).An attempt has been made to throw some light on the cause of this difference.