← Back to Search
A Rhodium-catalyzed Transannulation Of N-(per)fluoroalkyl-1,2,3-triazoles Under Microwave Conditions - A General Route To N-(per)fluoroalkyl-substituted Five-membered Heterocycles.
Vladimir A Motornov, Athanasios Markos, P. Beier
Published 2018 · Chemistry, Medicine
Download PDFAnalyze on Scholarcy
A rhodium-catalyzed transannulation via ring-opening of N-(per)fluoroalkyl-substituted 1,2,3-triazoles followed by cycloaddition with different nitriles, enol ethers, isocyanates and silyl ketene acetals under microwave heating provided a highly efficient route to previously unreported N-(per)fluoroalkyl-substituted imidazoles, pyrroles, imidazolones and pyrrolones, respectively. These reactions were found to be applicable to the synthesis of a variety of 5-membered heterocycles bearing different (per)fluoroalkyl substituents as well as both electron-donating and electron-withdrawing groups attached to the heterocyclic core.
This paper references
Perfluoroalkyl isocyanates: general synthesis by the pyrolysis of disilyl esters of hydroxamic acids
W. J. Middleton (1984)
Direct electrophilic N-trifluoromethylation of azoles by a hypervalent iodine reagent.
Katrin Niedermann (2012)
Rhodium-catalyzed transannulation of 1,2,3-triazoles to polysubstituted pyrroles.
S. Rajasekar (2014)
Facile synthesis of pyrroles via Rh(II)-catalyzed transannulation of 1-tosyl-1,2,3-triazoles with silyl or alkyl enol ethers
Juan Feng (2014)
Rhodium(II)‐Stabilized Carbenoids Containing Both Donor and Acceptor Substituents
H. Davies (2005)
Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes.
Buddhadeb Chattopadhyay (2011)
Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.
Tony Horneff (2008)
Organofluorine Compounds in Bilogy
P. V. Reddy (2015)
Generation of heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions and their reactions with electrophiles: heteroaryl- and heteroarylium-N-difluoromethyl trimethylsilanes and a new heteroaryl-N-trifluoromethane
G. Bissky (2001)
Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.
S. Chuprakov (2007)
Convenient Access to α-Fluorinated Alkylammonium Salts.
Amanda F. Baxter (2015)
Naturally Occurring and Synthetic Imidazoles: Their Chemistry and Their Biological Activities
L. Luca (2006)
Imidazole and benzimidazole derivatives as chemotherapeutic agents.
M. Boiani (2005)
Catalytic asymmetric synthesis of pyrroloindolines via a rhodium(II)-catalyzed annulation of indoles.
J. Spangler (2013)
Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.
Buddhadeb Chattopadhyay (2012)
Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles.
H. Davies (2014)
Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines.
J. Yu (2017)
Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles.
M. Zibinsky (2011)
Heterocyclic AntitumorAntibiotics. Topics in Heterocyclic Chemistry
J. T. Gupton (2006)
Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench‐Stable Precursor (Me4N)SCF3
Thomas Scattolin (2017)
Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.
S. Chuprakov (2013)
Cu-catalyzed transannulation reaction of pyridotriazoles with terminal alkynes under aerobic conditions: efficient synthesis of indolizines† †Electronic supplementary information (ESI) available: Experimental procedures and characterization for new compounds are provided. See DOI: 10.1039/c4sc03358b
V. Helan (2015)
Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas.
Y. Zhou (2016)
Synthesis of tetrafluoroethylene- and tetrafluoroethyl-containing azides and their 1,3-dipolar cycloaddition as synthetic application.
S. Voltrová (2017)
Intramolecular dearomatizing [3 + 2] annulation of α-imino carbenoids with aryl rings furnishing 3,4-fused indole skeletons.
T. Miura (2014)
Synthesis of 3-pyrrolin-2-ones by rhodium-catalyzed transannulation of 1-sulfonyl-1,2,3-triazole with ketene silyl acetal.
Rui-Qiao Ran (2014)
Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).
Jiang Wang (2014)
Fluorine in medicinal chemistry and chemical biology
I. Ojima (2009)
Fluorine in medicinal chemistry.
Sophie Purser (2008)
Modern Fluoroorganic Chemistry, Wiley-VCH
P. Kirsch (2013)
Topics in heterocyclic chemistry
R. N. Castle (1969)
Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.
Zsófia E. Blastik (2017)
This paper is referenced by
Construction of N‐CF2H, N‐CF3, and N‐CH2CF3 Motifs
T. Milcent (2020)
Stereoselective Synthesis of (Z)-β-Enamido Triflates and Fluorosulfonates from N-Fluoroalkylated Triazoles.
Athanasios Markos (2019)
The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2018
J. W. Herndon (2019)
General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles
Vladimir A Motornov (2019)
Synthesis, Stability and Reactivity of α-Fluorinated Azidoalkanes.
Olga Bakhanovich (2019)
Azidofluoromethane: synthesis, stability and reactivity in [3 + 2] cycloadditions
S. Voltrová (2020)