23 research outputs found
The versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties
Full text linkThe versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties Part 4*. Ionic liquids and reagents (Selectfluor, DABSO) derived from DABCO, DABCO as piperazine source
Full text linkQuaternary <i>N</i>-(2-Pyridyl)-DABCO Salts: One-Pot in Situ Formation from Pyridine-<i>N</i>-oxides and Reactions with Nucleophiles: A Mild and Selective Route to Substituted <i>N</i>-(2-Pyridyl)-<i>N</i>′-ethylpiperazines
Full text linkArynes, diaryliodonium salts and azine N-oxides in transition metal-free electrophilic N-arylation
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The main approach to the synthesis of aromatic and heteroaromatic amines is based on palladium- and copper-catalyzed N-arylation reactions. Although these methods are highly efficient and provide extensive opportunities for the synthesis of (het)arylamines with various structures and properties, they have some limitations related to the catalysts used and reaction conditions. This review addresses alternative approaches to N-(het)arylation that have been extensively developed in the past decade and are based on the use of arynes, diaryliodonium salts and azine N-oxides as electrophilic (het)arylating agents. Because of mild reaction conditions and no need for catalysts and strong bases, these N-(het)arylation methods are attractive for various synthetic applications and open up new possibilities for the preparation of valuable organic compounds inaccessible via traditional catalytic methods. The attention is focussed on publications of the last decade. The bibliography includes 112 references.</jats:p
The versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties Part 1. Catalysis of Morita–Baylis–Hillman and Knoevenagel reactions
Full text linkFrom Pyridine-<i>N</i>-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy
Full text linkThe versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties Part 2*. Catalysis of Michael and Biginelli reactions and nucleophilic addition at C=X and C≡X bonds
Full text linkSynthesis of Quinoline-2-thiones by Selective Deoxygenative C<i>–</i>H/C<i>–</i>S Functionalization of Quinoline <i>N</i>-Oxides with Thiourea
Full text linkA Thiol-Free Route to Alkyl Aryl Thioethers
No full textMost existing methods for the synthesis of alkyl aryl
thioethers
require the use of mercaptans as the starting materials, which comes
with practical limitations. Reactions of diaryliodonium salts with
xanthate salts, easily prepared from the corresponding alcohols and
CS2, under the developed conditions represent an operationally
simple, thiol-free method for the synthesis of these valuable compounds.
The protocol features high functional group tolerance and can be applied
to the late-stage C–H functionalization and for the introduction
of a CD3S group
A Thiol-Free Route to Alkyl Aryl Thioethers
No full textMost existing methods for the synthesis of alkyl aryl
thioethers
require the use of mercaptans as the starting materials, which comes
with practical limitations. Reactions of diaryliodonium salts with
xanthate salts, easily prepared from the corresponding alcohols and
CS2, under the developed conditions represent an operationally
simple, thiol-free method for the synthesis of these valuable compounds.
The protocol features high functional group tolerance and can be applied
to the late-stage C–H functionalization and for the introduction
of a CD3S group
