Tetrabutylammonium fluoride trihydrate is a mild base used in reactions like aldol-type condensation reactions, Michael-type reactions, ring-opening reactions. Its is also used as a promoter in cross-coupling reactions and cyclization of carbocycles and heterocycles.参考sigma
application：
Reactant for:
Preparation of deprotecting agents in preparation of cellulose derivatives
Synthesis of lipophilic peptides for DNA transfections in vivo
Dehydrobromination reactions
Tetrabutylammonium fluoride trihydrate can be used as a base:
For the dehydrobromination of vinyl bromides to terminal acetylenes.
In the conversion of 1,1-dibromo-1-alkenes to terminal alkynes via Corey–Fuchs reaction.
In Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryltrialkoxysilanes in the presence of a palladium catalyst.
It can be used to catalyze ethynylation of quinolines and isoquinolines using calcium carbide in aqueous N,N-dimethylacetamide.
1.Wen Huang, Guang Yang, Qingbo Xu, Meixiao Zhan, Lijuan Yao, Honghui Li, Fengfeng Xiao, Zirun Chen, Xiaoguang Zhao, Wenting Li, Wei Zhao, Fujun Zhang, Yong Li, Ligong Lu. (2023) One-Pot, Open-Air Synthesis of Flexible and Degradable Multifunctional Polymer Composites with Adhesion, Water Resistance, Self-Healing, Facile Drug Loading, and Sustained Release Properties. MACROMOLECULAR BIOSCIENCE, 23 (4):(2200442). [PMID:36623250][10.1002/mabi.202200442]
2.Jianhui Jia, Jian-Bo Chen, Jianglong Du, Cheng Lian, Silong Xu, Honglai Liu, Shichun Li, Yu Liu. (2022) Self-assembled core–shell clusters in deep eutectic solvents based on tetra-n-alkylammonium cations for high dissolution of strongly hydrogen-bonded small molecules. JOURNAL OF COLLOID AND INTERFACE SCIENCE, 628 (426). [PMID:35932679][10.1016/j.jcis.2022.07.140]
3.Lei Miao, Yuanyuan Tu, Yang Yang, Shudong Lin, Jiwen Hu, Min Zhang, Yue Li, Fei Li, Yangmiao Mo. (2017) Robust Stimuli-Responsive Membranes Prepared from a Blend of Polysulfone and a Graft Copolymer Bearing Binary Side Chains with Thermo- and pH-Responsive Switching Behavior. CHEMISTRY-A EUROPEAN JOURNAL, 23 (32):(7737-7747). [PMID:28332741][10.1002/chem.201605263]
References
1.Delia López-Velázquez,Armando R Hernández-Sosa,Ernesto Pérez. (2015-04-11) Effect of the degree of substitution in the transition temperatures and hydrophobicity of hydroxypropyl cellulose esters.. Carbohydrate polymers, 125 (224-231). [PMID:25857978]
2.Wen Huang, Guang Yang, Qingbo Xu, Meixiao Zhan, Lijuan Yao, Honghui Li, Fengfeng Xiao, Zirun Chen, Xiaoguang Zhao, Wenting Li, Wei Zhao, Fujun Zhang, Yong Li, Ligong Lu. (2023) One-Pot, Open-Air Synthesis of Flexible and Degradable Multifunctional Polymer Composites with Adhesion, Water Resistance, Self-Healing, Facile Drug Loading, and Sustained Release Properties. MACROMOLECULAR BIOSCIENCE, 23 (4):(2200442). [PMID:36623250][10.1002/mabi.202200442]
3.Jianhui Jia, Jian-Bo Chen, Jianglong Du, Cheng Lian, Silong Xu, Honglai Liu, Shichun Li, Yu Liu. (2022) Self-assembled core–shell clusters in deep eutectic solvents based on tetra-n-alkylammonium cations for high dissolution of strongly hydrogen-bonded small molecules. JOURNAL OF COLLOID AND INTERFACE SCIENCE, 628 (426). [PMID:35932679][10.1016/j.jcis.2022.07.140]
4.Lei Miao, Yuanyuan Tu, Yang Yang, Shudong Lin, Jiwen Hu, Min Zhang, Yue Li, Fei Li, Yangmiao Mo. (2017) Robust Stimuli-Responsive Membranes Prepared from a Blend of Polysulfone and a Graft Copolymer Bearing Binary Side Chains with Thermo- and pH-Responsive Switching Behavior. CHEMISTRY-A EUROPEAN JOURNAL, 23 (32):(7737-7747). [PMID:28332741][10.1002/chem.201605263]
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