188908-91-0

Upstream product

• 13781-53-8 (thiophen-3-yl)acetonitrile 
• 74-88-4 methyl iodide 
• 20893-30-5 2-cyanomethylthiophene 
• 67237-53-0 3-ethynylthiophene 
• 14906-59-3 4-cyanopyridine N-oxide 
• 872-31-1 3-Bromothiophene 
• 1617-17-0 2-chlorpropionitrile 

Downstream Products

• 1429308-78-0 4-methyl-9a-phenyl-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one 

Relevant academic research and scientific papers

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Catalytic asymmetric protonation of silyl ketene imines

An efficient catalytic and highly enantioselective protonation of silyl ketene imines is described. The reaction is catalyzed by the chiral phosphoric acids TRIP or STRIP in the presence of a stoichiometric amount of methanol as the proton source and silyl acceptor. A variety of substituted racemic silyl ketene imines have been transformed into highly enantioenriched nitriles.

A cascade approach to fused indolizinones through Lewis acid-copper(i) relay catalysis

A relay catalytic cascade process involving Lewis acid triggered ring-opening of cyclopropyl ketones with nitriles, the copper(i)-catalyzed Ritter process, and acid-promoted N-acyliminium ion cyclization is described, which efficiently provides thieno-, furano-, and benzo-indolizinones in moderate to good yields. The Royal Society of Chemistry 2013.

Quinoline and naphthyridine carboxylic acid antibacterials

Compounds having formula (I) or pharmaceutically acceptable salts or prodrugs thereof, are useful as antibacterial agents.

Nickel-catalysed electrochemical coupling of 2- and 3-bromothiophene with alkyl and alkenyl halides

2- or 3-bromothiophene are efficiently coupled with activated alkyl chlorides (α-chloroesters, α-chloroketones, α-chloronitriles), benzyl chloride or vinyl halides, in a one step electrochemical reaction, using the sacrificial anode process and catalysis by NiBr2-2,2'-bipyridine (bipy).