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Upstream product

• 53458-16-5 1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one 
• 62-53-3 aniline 
• 459-57-4 4-fluorobenzaldehyde 
• 5216-31-9 1,2-bis(4-fluorophenyl)acetylene 
• 59-88-1 phenylhydrazine hydrochloride 
• 114-83-0 1-acetyl-2-phenylhydrazine 
• 615-43-0 2-iodophenylamine 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 52670-38-9 2-ethynylaniline 
• 352-34-1 4-fluoro-1-iodobenzene 
• 143360-93-4 N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 103-71-9 phenyl isocyanate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.

Synthesis of Unprotected and Highly Substituted Indoles by the Ruthenium(II)-Catalyzed Reaction of Phenyl Isocyanates with Diaryl/Diheteroaryl Alkynes/Ethyl-3-phenyl Propiolates

A one-pot transformation has been developed for the synthesis of unprotected and highly substituted indoles by an in situ installed carbamide-directed Ru(II)-catalyzed intermolecular oxidative annulation of phenyl isocyanates with diaryl/diheteroaryl alkynes/ethyl phenyl propiolates in the presence of Cu(OAc)2·H2O as an oxidant and AgSbF6 as an additive at 120 °C within 3 h.

Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines

The transition-metal-free and temperature-dependent highly selective reaction of arynes with 2H-azirines allowing the synthesis of either N-unsubstituted or N-arylindoles has been developed. At 60 °C, arynes generated from 2-(trimethylsilyl)aryl triflates smoothly insert into 2H-azirines to form 2,3-diarylindoles with high selectivity. Interestingly, when the reaction was performed at -10 °C, the selectivity was switched to the formation of 1,2,3-triarylindoles in good yields.

Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage

A redox-neutral cobalt(III)-catalyzed synthetic approach for the direct synthesis of unprotected indoles showcasing an N-N bond cleavage is reported. The herein newly introduced Boc-protected hydrazines establish a beneficial addition to the limited portfolio of oxidizing directing groups for cobalt(III) catalysis. Moreover, the developed catalytic methodology tolerates a good variety of functional groups.

A kind of high-efficient synthetic indole and isoquinoline derivatives (by machine translation)

The invention discloses a substituted indole and isoquinoline preparation method, which belongs to the technical field of organic chemical synthesis. This method adopts the oxygen as the oxidizing agent, various substituents substituted alkyne starting material of the aromatic amine or [...] , by transition metal-catalyzed, get containing indole or isoquinoline compound of the structure. The reaction raw material, oxidizing agent and cheap and easily obtained catalyst, synthesis technique is simple, which greatly reduces the cost of synthesizing; mild reaction conditions, high yield, easy industrialization; reaction raw materials and catalyst cleaning non-toxic, small pollution to the environment. Such compounds and their derivatives as an important fine chemicals, in the medical, agricultural chemicals, perfume and widely used photoelectric and other industries. (by machine translation)

Rhodium(III)-Catalyzed Redox-Neutral C-H Annulation of Arylnitrones and Alkynes for the Synthesis of Indole Derivatives

By using a nitrone as the oxidizing directing group, a mild, practical and efficient rhodium(III)-catalyzed C-H functionalization for the synthesis of indole derivatives has been developed. This reaction obviates the need for an external oxidant and shows good functional group tolerance. The employment of a sterically hindered Mes group on the carbon center of the nitrone is crucial to produce indoles in high yield.

Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group

A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.

Rhodium(III)-catalyzed c-h activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group

An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for RhIII-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and Ci￡O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DGauto). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DGauto strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated. Copyright

Rh-Catalyzed oxidative C-H activation/annulation: Converting anilines to indoles using molecular oxygen as the sole oxidant

A practical and efficient Rh(iii)-catalyzed aerobic C-H activation has been developed for the facile synthesis of a broad range of indoles from simple anilines and alkynes. The protocol could be conducted under mild conditions and used environmentally friendly oxygen as the sole clear oxidant.

Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage

Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright