127473-29-4

Upstream product

• 501-65-5 diphenyl acetylene 
• 35292-54-7 N-methyl-N-(p-methoxyphenyl)hydrazine 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 940-11-4 N-methyl-N-nitroso-p-anisidine 

Downstream Products

• 127473-41-0 5-(β-D-glucopyranosyloxy)-2,3-diphenylindole 
• 127473-40-9 2,3-diphenyl-5-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)indole 
• 127473-31-8 1-methyl-2,3-diphenyl-5-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)indole 
• 127473-32-9 1-Methyl-2,3-diphenyl-5-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-1H-indole 
• 127473-28-3 5-hydroxy-1-methyl-2,3-diphenylindole 

Relevant academic research and scientific papers

Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles

A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.

One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives

The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.

Traceless directing strategy: Efficient synthesis of N-alkyl indoles via redox-neutral C-H activation

A general protocol for the synthesis of N-alkyl indoles has been developed via a redox neutral C-H activation strategy using a traceless nitroso directing group. A broad scope of substituted N-alkyl indoles has been prepared in good to excellent yields using a very simple Rh catalyst system in the absence of an external oxidant or any other additive. Good to excellent regioselectivity has been achieved for asymmetrically disubstituted acetylenes.