Oxidative cross-coupling of secondary phosphine chalcogenides with amino alcohols and aminophenols: aspects of the reaction chemoselectivity

2021 ◽  
Author(s):  
Kseniya O. Khrapova ◽  
Anton A. Telezhkin ◽  
Pavel A. Volkov ◽  
Lyudmila I. Larina ◽  
Dmitry V. Pavlov ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Amino Alcohols ◽  
Similar Reaction ◽  
Secondary Phosphine ◽  
Oh Groups ◽  
Secondary Phosphine Chalcogenides ◽  
Primary Amino ◽  
Phosphine Chalcogenides

Phosphine chalcogenides react with primary amino alcohols in a CCl4/Et3N system to chemoselectively deliver chalcogenophosphinic acids amides with free OH groups. Similar reaction for aminophenols gives exclusively chalcogenophosphinic O-esters.

scholarly journals Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6824
Author(s):  
Boris A. Trofimov ◽  
Pavel A. Volkov ◽  
Anton A. Telezhkin
Keyword(s):  
Nucleophilic Addition ◽  
Pyridine Ring ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Metal Free ◽  
Secondary Phosphine Chalcogenides ◽  
Heterocyclic Moiety ◽  
Acid Esters ◽  
Phosphine Chalcogenides

Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/P-nucleophiles (phosphine chalcogenides, H-phosphonates) are reviewed. Special attention is focused on a SNH reaction of the regioselective cross-coupling of pyridines with secondary phosphine chalcogenides triggered by acylacetylenes to give 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as three-modal adjuvants (i) activating the pyridine ring towards P-nucleophiles, (ii) deprotonating the P-H bond and (iii) facilitating the nucleophilic addition of the P-centered anion to a heterocyclic moiety followed by the release of the selectively reduced acetylenes (E-alkenes).

Oxidative Cross-Coupling of Cysteamine with Secondary Phosphine Chalcogenides: Aspects of Reaction Chemoselectivity

2020 ◽  
Vol 490 (1) ◽  
pp. 11-15
Author(s):  
K. O. Khrapova ◽  
N. K. Gusarova ◽  
A. A. Telezhkin ◽  
P. A. Volkov ◽  
N. I. Ivanova ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Secondary Phosphine Chalcogenides ◽  
Phosphine Chalcogenides

Chemoselective Cross-Coupling of Secondary Phosphine Chalcogenides with Aminophenols: Synthesis of Aminophenylchalcogenophosphinic Acids O-Esters

2018 ◽  
Vol 88 (10) ◽  
pp. 2223-2226
Author(s):  
K. O. Khrapova ◽  
P. A. Volkov ◽  
N. I. Ivanova ◽  
A. A. Telezhkin ◽  
N. K. Gusarova ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Secondary Phosphine Chalcogenides ◽  
Phosphine Chalcogenides

Oxidative metal-free cross-coupling of secondary phosphine chalcogenides and benzenediols: Synthesis of phosphinochalcogenoic O-diesters

2012 ◽  
Vol 23 (4) ◽  
pp. 322-328 ◽  
Author(s):  
Nina K. Gusarova ◽  
Pavel A. Volkov ◽  
Nina I. Ivanova ◽  
Ludmila I. Larina ◽  
Boris A. Trofimov
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Metal Free ◽  
Secondary Phosphine Chalcogenides ◽  
Phosphine Chalcogenides

Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants

2018 ◽  
Vol 54 (27) ◽  
pp. 3371-3374 ◽  
Author(s):  
Boris A. Trofimov ◽  
Pavel A. Volkov ◽  
Kseniya O. Khrapova ◽  
Anton A. Telezhkin ◽  
Nina I. Ivanova ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Metal Free ◽  
Mild Conditions ◽  
Secondary Phosphine Chalcogenides ◽  
Site Selective ◽  
Phosphine Chalcogenides

Pyridines are easily cross-coupled with secondary phosphine chalcogenides in the presence of acylphenylacetylenes under mild conditions to afford 4-chalcogenophosphorylpyridines.

ChemInform Abstract: Oxidative Metal-Free Cross-Coupling of Secondary Phosphine Chalcogenides and Benzenediols: Synthesis of Phosphinochalcogenoic O-Diesters.

ChemInform ◽  
2012 ◽  
Vol 43 (46) ◽  
pp. no-no
Author(s):  
Nina K. Gusarova ◽  
Pavel A. Volkov ◽  
Nina I. Ivanova ◽  
Ludmila I. Larina ◽  
Boris A. Trofimov
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Metal Free ◽  
Secondary Phosphine Chalcogenides ◽  
Phosphine Chalcogenides

An Expedient Access to γ-Ketophosphine Chalcogenides via the Chemo- and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ-Ethylenic Ketones

2015 ◽  
Vol 26 (6) ◽  
pp. 455-462 ◽  
Author(s):  
Alexander V. Artem'ev ◽  
Svetlana F. Malysheva ◽  
Nataliya A. Belogorlova ◽  
Nadezhda I. Protzuk ◽  
Alexander I. Albanov ◽  
...  
Keyword(s):  
Secondary Phosphine ◽  
Secondary Phosphine Chalcogenides ◽  
Regioselective Addition ◽  
Phosphine Chalcogenides

One-pot reductive N-vinylation and C(4)-phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides

2015 ◽  
Vol 56 (33) ◽  
pp. 4804-4806 ◽  
Author(s):  
Nina K. Gusarova ◽  
Pavel A. Volkov ◽  
Nina I. Ivanova ◽  
Svetlana N. Arbuzova ◽  
Kseniya O. Khrapova ◽  
...  
Keyword(s):  
Secondary Phosphine ◽  
One Pot ◽  
Secondary Phosphine Chalcogenides ◽  
Alkyl Propiolates ◽  
Phosphine Chalcogenides
Sign in / Sign up

Export Citation Format

Share Document