Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes

Lu, Zhichao; Hennis, Olivia; Gentry, Joseph; Xu, Bo; Hammond, Gerald B.

doi:10.1021/acs.orglett.0c01395

Cited by 18 publications

(8 citation statements)

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N -Methacryloyl-2-phenylbenzoimidazole 1a–1l and 1q were prepared according to Lei’s method ( 1a – 1e, 1j were known compounds ,, ). N -Methacryloyl-2-phenylindole 1m–1p were prepared according to Kim’s method ( 1m was known compounds). − N -Hydroxyphthalimide esters 2a–2l were all known compounds and prepared according to Baran’s method. ,,,− The aryldiazonium tetrafluoroborates 2m–2q were all known compounds and prepared according to our previous work. − …”

Section: Methodsmentioning

confidence: 99%

Aromatic Ketone-Catalyzed Photochemical Synthesis of Imidazo-isoquinolinone Derivatives

Zhao

Hammond

2021

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 99%

Aromatic Ketone-Catalyzed Photochemical Synthesis of Imidazo-isoquinolinone Derivatives

Zhao

Hammond

2021

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…As an important structural motif of nitrogen‐containing compounds, azo compounds are not only important synthetic colorants in the dye industry, but also used as indicators or food additives [7] . The electrophilic diazonium function allows the addition of nucleophiles to provide azo compounds, and the diazonium salts substituted with electron‐withdrawing substituents show high chemical selectivity [8] . When the aryl diazonium salt undergoes a free radical mechanism reaction, the electron donating substitution generally obtains a higher yield [9] .…”

Section: Methodsmentioning

confidence: 99%

Paired Electrosynthesis of Aromatic Azo Compounds from Aryl Diazonium Salts with Pyrroles or Indoles

Yao

et al. 2021

Adv Synth Catal

View full text Add to dashboard Cite

An efficient paired electrosynthesis of functionalized aromatic azo compounds through a diazenyl radical pathway has been developed. The paired electrolysis simultaneously uses the anode and cathode reactions to avoid the electricity expense of oxidation/reduction of sacrificial substances, thereby maximizing energy efficiency and achieving high atom economy. The in vitro cytotoxicity of all compounds was evaluated against four cancer cell lines by MTT assay. Results showed that the aromatic azo compounds exhibited good antitumor activity in vitro, and one of the compounds induced tumor cell apoptosis.

show abstract

“… (a) Photocatalytic [92] and (b) TBOAc‐promoted [93] azo‐trifluoromethylations with aryldiazonium salts.…”

Section: Amino‐trifluoromethylationmentioning

confidence: 99%

Evolution and Future of Hetero‐ and Hydro‐Trifluoromethylations of Unsaturated C−C Bonds

et al. 2023

View full text Add to dashboard Cite

The difunctionalizative trifluoromethylation of unsaturated CÀ C bonds is a highly useful and efficient method for the synthesis of trifluoromethyl compounds with attractive architectures from simple feedstocks, allowing the introduction of the CF 3 group along with a wide variety of substituents either inter-or intramolecularly. Given that trifluoromethyl molecules are increasingly used as promising bioactive species in the design of new drugs and agrochemicals, difunctionalizative trifluoromethylation has been extensively studied during the last decade. This review focuses on reactions proceeding via the simultaneous formation of CÀ heteroatom (O, N, S, Se, B) and CÀ H bonds, as these reactions provide useful CF 3 group-containing building blocks. To identify the trends and prospects of the evolution of this methodology, we systematically describe the variants of these types of reactions and provide a more general view of reaction conditions, modes, and mechanisms. The presented comprehensive survey enables the categorization of reactions into those that are synthetically mature and those with room for further development. 1.Shintaro Kawamura completed his Ph.D. at Kyoto University in 2013 under the supervision of Prof. Masaharu Nakamura. Since 2012, he has worked in Prof. Mikiko Sodeoka's group at RIKEN. He was promoted from a postdoctoral researcher to a Research Scientist (2017) and then to a Senior Research Scientist (2021) at RIK-EN. Dr. Kawamura's research interests include fluoroalkylation reactions based on the precise reactivity control of radical species. Pablo Barrio completed his Ph.D. at the University of Oviedo in 2007 under the supervision of Prof. Barluenga. After a postdoctoral role in the group of Prof. Carreira at ETH Zurich, he joined the group of Prof. Fustero in 2009 as a Juan de la Cierva Fellow, working for several years in the field of organofluorine chemistry. In 2018, he moved to Oviedo as a Ramón y Cajal Fellow, joining the Selective Organic Synthesis (SOS) group. Dr. Barrio's research interests include gold catalysis. Santos Fustero studied Chemistry at the University of Zaragoza, where he obtained his B.S. and Ph.D. under the supervision of Prof. Barluenga and Prof. Gotor. He spent two years as a postdoctoral research associate at Prof. Lehmkuhl's laboratory at Max-Planck-Institut für Kohlenforschung in Mülheim an der Ruhr, Germany. In 1983, he became Associate Professor at the University of Oviedo, Spain, and was promoted to Full Professor at the University of Valencia in 1990. In 2005, he became a research group leader at Centro de Investigación Príncipe Felipe in Valencia. Prof. Fustero's research interests include organofluorine and medicinal chemistry, organocatalysis, heterocyclic chemistry, and new reaction methodologies. Jorge Escorihuela received his Ph.D. in Chemistry at Universitat Jaume I (Castellon, Spain) in 2009. After a postdoctoral stage at Universitat Politècnica de València (UPV), he worked at Wageningen University and Research (the Netherlands) with Prof. Zuilho...

show abstract

Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes

Cited by 18 publications

References 66 publications

Aromatic Ketone-Catalyzed Photochemical Synthesis of Imidazo-isoquinolinone Derivatives

Aromatic Ketone-Catalyzed Photochemical Synthesis of Imidazo-isoquinolinone Derivatives

Paired Electrosynthesis of Aromatic Azo Compounds from Aryl Diazonium Salts with Pyrroles or Indoles

Evolution and Future of Hetero‐ and Hydro‐Trifluoromethylations of Unsaturated C−C Bonds

Contact Info

Product

Resources

About