Phosphazene Base P<sub>4</sub>-<i>t</i>-Bu

Schwesinger, Reinhard; Kondo, Yoshinori

doi:10.1002/047084289x.rp150.pub2

Cited by 3 publications

(2 citation statements)

References 35 publications

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“…Improved activation systems are currently under development, including for the stronger P 4 - t -Bu superbase. 4 a ,39 The precatalyst systems have the potential to accelerate the discovery of new superbases, superbase-promoted applications and their use by a wider community. More broadly, the mechanistic ability to regulate superbase introduction to solutions presents a myriad of possibilities for improving or manipulating base-promoted reactivity, a prospect that we are currently pursuing in numerous contexts.…”

Section: Discussionmentioning

confidence: 99%

A strategy for the controllable generation of organic superbases from benchtop-stable salts

Sujansky,

Hoteling,

Bandar

2024

Chem. Sci.

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Section: Discussionmentioning

confidence: 99%

A strategy for the controllable generation of organic superbases from benchtop-stable salts

Sujansky,

Hoteling,

Bandar

2024

Chem. Sci.

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“…This would mainly be due to the formation of aggregates in the reaction mixture, probably coming from the non-miscibility of hexanesolvent in which P4t-Bu is commercially available-and DMF, or by the fact that the superbase is not soluble in DMF. 35 A screening of different solvents was performed (Table 4). Practically, hexane from the commercially available solution was removed under vacuum from the desired amount of P4t-Bu.…”

Section: Evaluation Of the Diastereoselectivity Of The Synthesis Of αmentioning

confidence: 99%

Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols

et al. 2019

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The-CHF2 moiety has shown a growing interest in pharmaceutical and agrochemical applications over the last few years. Its introduction is therefore a current research topic for organic chemists. Several groups have reported the synthesis of difluoromethylated compounds. However, the more challenging enantioselective introduction of the difluoromethyl group has been scarcely described yet. We recently developed a new strategy, based on the use of an enantiopure difluoromethyl sulfoxide used as chiral and traceless auxiliary, for the synthesis of highly enantioenriched αdifluoromethyl alcohols. 8 The first method developed in our laboratory aims to access highly stereoenriched α,α-difluoro-β-hydroxysulfoxides through the condensation of the enantiopure difluoromethyl sulfoxide on carbonyl derivatives. It is noteworthy that highly diastereo-and enantioenriched α,α-difluoro-β-hydroxysulfoxides can also be accessed after the diastereoselective reduction of highly enantioenriched α,α-difluoro-β-ketosulfoxides. Finally, the expected difluoromethyl-substituted alcohols can be obtained after removal of the chiral auxiliary with complete retention of stereoenrichment at carbon.

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Design of Exceptional Strong Organosuperbases Based on Iminophosphorane and Azaphosphiridine Derivatives: Harnessing Ring Strain and Aromaticity to Engineer Neutral Superbases

Saeidian

Barfinejad

2019

ChemistrySelect

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A new class of non-ionic organosuperbases was designed using iminophosphorane and azaphosphiridine frameworks, and their gas phase proton affinity (PA) and gas phase basicity (GB) were assessed by using density functional theory computations. The utilized strategy for tailoring the organosuperbases is based on stimulating of ring opening upon protonation bearing substituents which have the ability of positive charge delocalization. After protonation, most of the superbases formed positive aromatic rings (C 3 H 3 + and C 7 H 7 + ). This strategy led to the design of organobases with exceptional basicity in the range of 1013-1317 kJ mol À 1 . Five designed organosuperbases show the PA values > 1254 kJ mol À 1 , above the range of a hyperbase. To better comprehend the basicity of the compounds, the aromaticity indices (NICS and HOMA data) associated with the organosuperbases and their corresponding conjugate acids have been calculated and compared with each other.[a] Dr.

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Phosphazene Base P₄-t-Bu

Cited by 3 publications

References 35 publications

A strategy for the controllable generation of organic superbases from benchtop-stable salts

A strategy for the controllable generation of organic superbases from benchtop-stable salts

Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols

Design of Exceptional Strong Organosuperbases Based on Iminophosphorane and Azaphosphiridine Derivatives: Harnessing Ring Strain and Aromaticity to Engineer Neutral Superbases

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Phosphazene Base P4-t-Bu

Cited by 3 publications

References 35 publications

A strategy for the controllable generation of organic superbases from benchtop-stable salts

A strategy for the controllable generation of organic superbases from benchtop-stable salts

Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols

Design of Exceptional Strong Organosuperbases Based on Iminophosphorane and Azaphosphiridine Derivatives: Harnessing Ring Strain and Aromaticity to Engineer Neutral Superbases

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Phosphazene Base P₄-t-Bu