Reaction of ozone with five-membered hetarenes in a liquid phase

Andreev, P. Yu.

doi:10.1134/s1070427212090157

Cited by 6 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tetraphenyl cyclopentadiene was converted to the corresponding tetraphenyl pyridine 2aq in a single step in 44% yield. Functional groups, such as alkenes, alkynes, selenides, thioethers, thiophenes 62,63 , and indole 64 , which react with ozone readily, were all tolerated during the transformations. In the example of 2 v, a theoretical atom economy of 99.2% was realized.…”

Section: Resultsmentioning

confidence: 99%

Insertion of ammonia into alkenes to build aromatic N-heterocycles

Liu

2022

Nat Commun

View full text Add to dashboard Cite

Ammonia is one of the most abundant and simple nitrogen sources with decent stability and reactivity. Direct insertion of ammonia into a carbon skeleton is an ideal approach to building valuable N-heterocycles for extensive applications with unprecedented atom and step economy. Here, we show an electrochemical dehydrogenative method in which ammonia is inserted directly into alkenes to build aromatic N-heterocycles in a single step without the use of any external oxidant. This new approach achieves 98–99.2% atom economy with hydrogen as the only byproduct. Quinoline and pyridine with diverse substitutions are readily available. In this work, electrochemistry was used to drive a 4-electron oxidation reaction that is hard to access by other protocols, providing a parallel pathway to nitrene chemistry. In a tandem transformation that included three distinct electrochemical processes, the insertion of ammonia further showcased the tremendous potential to manipulate heterocycles derived from Hantzsch ester to diazine via pyridine and pyrrole.

show abstract

Section: Resultsmentioning

confidence: 99%

Insertion of ammonia into alkenes to build aromatic N-heterocycles

Liu

2022

Nat Commun

View full text Add to dashboard Cite

show abstract

“…n (Tetreau et al, 1972) 5 3-Hydroxy-2,5bis(hydroxymeth yl) furan 4.0E-11 o (Atkinson et al, 1983) 2.4E-18 o (Atkinson et al, 1983) 3.9E+09 p (Lilie, 1971) 1.0E+08 q (Wilkinson et al, 1995) 1.2E+03 r (Andreev, 2012) 1.4E+08 s (Kaur and Anastasio, 2018) References for the measured rate constants are indicated. Values indicated are at 298 K wherever available.…”

Section: Details Of the Technique Are Discussed Inmentioning

confidence: 99%