scholarly journals Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

2015 ◽  
Vol 11 ◽  
pp. 1985-1990 ◽  
Author(s):  
Svetlana F Malysheva ◽  
Alexander V Artem’ev ◽  
Nina K Gusarova ◽  
Nataliya A Belogorlova ◽  
Alexander I Albanov ◽  
...  
Keyword(s):  
Solvent Free ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Solvent Free Conditions ◽  
Vinyl Sulfides

Secondary phosphine oxides react with vinyl sulfides (both alkyl- and aryl-substituted sulfides) under aerobic and solvent-free conditions (80 °C, air, 7–30 h) to afford 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides in 70–93% yields.

Catalyst- and Solvent-Free Addition of the P–H Species to Alkenes and Alkynes: A Green Methodology for C–P Bond Formation

Synthesis ◽  
2017 ◽  
Vol 49 (21) ◽  
pp. 4783-4807 ◽  
Author(s):  
Boris Trofimov ◽  
Nina Gusarova ◽  
Nataliya Chernysheva
Keyword(s):  
Organophosphorus Compounds ◽  
Bond Formation ◽  
Solvent Free ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Secondary Phosphine Chalcogenides ◽  
Vinyl Sulfides ◽  
Radical Initiators ◽  
Phosphine Chalcogenides ◽  
Secondary Phosphines

Traditional methods for C–P bond formation via direct addition of P–H species to unsaturated compounds are usually implemented in the presence of base and metal catalysts or radical initiators in various organic solvents. During the last five years, a novel efficient and general catalyst/initiator- and solvent-free version of the hydrophosphination and hydrophosphinylation of multiple C–C bonds with H-phosphines and their chalcogenides has begun to develop and it is attracting growing attention. This approach corresponds to the recently emerged pot-, atom-, and step-economy (PASE) green paradigm. This review covers the literature on the synthesis of useful and in-demand organophosphorus compounds via catalyst- and solvent-free addition of P–H species to alkenes and alkynes.1 Introduction2 Addition of Secondary Phosphines to Alkenes3 Hydrophosphinylation of Alkenes with Secondary Phosphine Chalcogenides3.1 Oxidative Addition of Phosphine Oxides to Vinyl Sulfides3.2 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Alkenes3.3 Addition of Secondary Phosphine Sulfides and Phosphine Selenides to Divinyl Chalcogenides3.4 Hydrophosphinylation of Alkenes with Secondary Phosphine/Chalcogen Pair (Three-Component Reactions)4 Addition of Secondary Phosphines to Alkynes5 Addition of Secondary Phosphine Chalcogenides to Alkynes6 Conclusion

scholarly journals A “green” variation of the Hirao reaction: the P–C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc)2 catalyst under microwave and solvent-free conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (43) ◽  
pp. 22808-22816 ◽  
Author(s):  
György Keglevich ◽  
Erzsébet Jablonkai ◽  
László B. Balázs
Keyword(s):  
Solvent Free ◽  
Diethyl Phosphite ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Title Reaction ◽  
Solvent Free Conditions ◽  
Ligand Free

The general value of the title reaction affording diethyl arylphosphonates, alkyl diphenylphosphinates and tertiary phosphine oxides was demonstrated.

ChemInform Abstract: Synthesis of Vinyl Sulfides via Hydrothiolation of Alkynes Using Al2O3/KF under Solvent-Free Conditions.

ChemInform ◽  
2008 ◽  
Vol 39 (26) ◽  
Author(s):  
Marcio S. Silva ◽  
Renata G. Lara ◽  
Junior M. Marczewski ◽  
Raquel G. Jacob ◽  
Eder J. Lenardao ◽  
...  
Keyword(s):  
Solvent Free ◽  
Solvent Free Conditions ◽  
Vinyl Sulfides

Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides

Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2224-2232
Author(s):  
Boris A. Trofimov ◽  
Nina K. Gusarova ◽  
Nina I. Ivanova ◽  
Kseniya O. Khrapova ◽  
Pavel A. Volkov ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Green Chemistry ◽  
Green Synthesis ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Solvent Free ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Intramolecular Hydrogen ◽  
Solvent Free Reaction

Tertiary α-hydroxyphosphine oxides have been synthesized via the catalyst- and solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20–62 °C in near to 96–98% yield. The developed method meets the requirements of green chemistry and the PASE (pot, atom, step economy) paradigm. According to quantum-chemical calculations at the B3LYP/6-311++G(d,p) level, the synthesized hydroxyphosphine oxides feature a weak (≈3 kcal·mol–1) O−H···O=P intramolecular hydrogen bond.

Non-catalyzed addition of secondary phosphine chalcogenides to divinyl chalcogenides under solvent-free conditions

2016 ◽  
Vol 37 (5) ◽  
pp. 488-500
Author(s):  
Nina K. Gusarova ◽  
Nataliya A. Chernysheva ◽  
Svetlana V. Yas’ko ◽  
Lyudmila V. Klyba ◽  
Boris A. Trofimov
Keyword(s):  
Solvent Free ◽  
Secondary Phosphine ◽  
Secondary Phosphine Chalcogenides ◽  
Solvent Free Conditions ◽  
Phosphine Chalcogenides

Synthesis of vinyl sulfides via hydrothiolation of alkynes using Al2O3/KF under solvent-free conditions

2008 ◽  
Vol 49 (12) ◽  
pp. 1927-1930 ◽  
Author(s):  
Márcio S. Silva ◽  
Renata G. Lara ◽  
Júnior M. Marczewski ◽  
Raquel G. Jacob ◽  
Eder J. Lenardão ◽  
...  
Keyword(s):  
Solvent Free ◽  
Solvent Free Conditions ◽  
Vinyl Sulfides

ChemInform Abstract: Aerobic Addition of Secondary Phosphine Oxides to Vinyl Sulfides: A Shortcut to 1-Hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine Oxides.

ChemInform ◽  
2015 ◽  
Vol 46 (52) ◽  
pp. no-no
Author(s):  
Svetlana F Malysheva ◽  
Alexander V. Artem'ev ◽  
Nina K. Gusarova ◽  
Nataliya A. Belogorlova ◽  
Alexander I. Albanov ◽  
...  
Keyword(s):  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Vinyl Sulfides
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