13 research outputs found
Aromás és heteroaromás vegyületek funkcionalizálása rézkatalizált átalakításban és hipervalens jodóniumsók segítségével
Stereoselective Direct N‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
The availability and synthesis of fluorinated enamine derivatives such as N-(3,3,3-trifluoropropenyl) heterocycles are challenging, especially through direct functionalization of the heterocyclic scaffold. Herein, a stereoselective N-trifluoropropenylation method based on the use of a bench-stable trifluoropropenyl iodonium salt is described. This reagent enables the straightforward trifluoropropenylation of various N-heterocycles under mild reaction conditions, providing trifluoromethyl enamine type moieties with high stereoselectivity and efficiency
Efficient Copper-Catalyzed Trifluoromethylation of Aromatic and Heteroaromatic Iodides: The Beneficial Anchoring Effect of Borates
Efficient copper
-
catalyzed trifluoromethylation of aromatic iodides was achieved with
TMSCF
3
in the presence of
trimethoxyborane. The Lewis acid was used to anchor the in situ generated trifluoromethyl anion and suppress its rapid decomp
os
i-
tion. Broad applicability of the new trifluoromethylating reaction was demonstrated in the functionali
zation of different aromatic
and heteroaro
matic iodides
Z‐Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium reagents in Palladium‐Catalyzed Directed C‐H Activation
Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles
Development of Ni-Ir Dual Photocatalytic Liebeskind-coupling of Sulfonium Salts for the Synthesis of 2-benzylpyrrolidines
Understanding and Exploitation of Neighboring Heteroatom Effect for the Mild N-arylation of Heterocycles with Diaryliodonium Salts under Aqueous Conditions: A Theoretical and Experimental Mechanistic Study.
The mechanism of
arylation of N-heterocycles with unsymmetric diaryliodonium
salts is elucidated. The fast and efficient N-arylation reaction is
interpreted in terms of the bifunctionality of the substrate: The
consecutive actions of properly oriented Lewis base and Brønsted
acid centers in sufficient proximity result in the fast and efficient
N-arylation. The mechanistic picture points to a promising synthetic
strategy where suitably positioned nucleophilic and acidic centers
enable functionalization, and it is tested experimentally
Understanding and Exploitation of Neighboring Heteroatom Effect for the Mild NArylation of Heterocycles with Diaryliodonium Salts under Aqueous Conditions: A Theoretical and Experimental Mechanistic Study
Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts
A new synthetic method was developed for the
N-arylation of pyrazoles using diaryliodonium salts. The
transformation does not require any transition-metal catalyst
and provides the desired N-arylpyrazoles rapidly
under mild reaction condition in the presence of aqueous
ammonia solution as a mild base without the use of inert
atmosphere. The chemoselectivity of unsymmetric diaryliodonium
salts was also explored with large number of
examples