2,2,6,6-Tetramethylpiperidinium triflate (TMPT): a highly selective and self-separated catalyst for esterification

[Display omitted] •Green and practical synthetic approaches with easy operation.•Excellent activity and selectivity.•Homogeneous catalyst with a self-separation feature.•The catalyst is reusable up to ten times without any significant loss of activity. An eco-friendly and readily accessible 2,2,6,6-...

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Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 44; pp. 4905 - 4909
Main Authors Gao, Lan, Liu, Taoping, Tao, Xiaochun, Huang, Yongmin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.11.2016
Elsevier
Subjects
Alkyl piperidinium sulfonates
Chemistry
Chemistry, Organic
Esterification
Physical Sciences
Science & Technology
Selectivity
Self-separation
Steric hindrance
Alkyl piperidinium sulfonates
Steric hindrance
Selectivity
Esterification
Self-separation
SULFONIC-ACID
EQUIMOLAR AMOUNTS
TRANSESTERIFICATION
RECYCLABLE ORGANOCATALYSTS
ALCOHOLS
EFFICIENT CATALYST
SO3H
BASE STRENGTHS
NH2
CARBOXYLIC-ACIDS
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Summary:[Display omitted] •Green and practical synthetic approaches with easy operation.•Excellent activity and selectivity.•Homogeneous catalyst with a self-separation feature.•The catalyst is reusable up to ten times without any significant loss of activity. An eco-friendly and readily accessible 2,2,6,6-tetramethylpiperidinium triflate was found as highly-selective and self-separated catalyst for esterification under solvent-free condition. The X-ray crystallography revealed that it formed a ‘hydrophobic wall’ which could effectively eliminate the generated water from the reactive sites. Moreover, it could precipitate from the reaction system with excellent recovery ratio (>99%) and be reused for ten times without any significant loss of activity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.09.061