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Keywords = organotrifluoroborate

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8 pages, 887 KiB  
Communication
Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts
by Kayla M. Fisher and Yuri Bolshan
Catalysts 2016, 6(7), 94; https://doi.org/10.3390/catal6070094 - 25 Jun 2016
Cited by 5 | Viewed by 6524
Abstract
Metal-free transformations of organotrifluoroborates are advantageous since they avoid the use of frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving potassium trifluoroborate salts have emerged as an alternative to metal-catalyzed protocols. However, the drawbacks to these methods are that they rely [...] Read more.
Metal-free transformations of organotrifluoroborates are advantageous since they avoid the use of frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving potassium trifluoroborate salts have emerged as an alternative to metal-catalyzed protocols. However, the drawbacks to these methods are that they rely on the generation of unstable boron dihalide species, thereby resulting in low functional group tolerance. Recently, we discovered that in the presence of a Brønsted acid, trifluoroborate salts react rapidly with in situ generated oxocarbenium ions. Here, we report Brønsted acid-catalyzed direct substitution of 2-ethoxytetrahydrofuran using potassium trifluoroborate salts. The reaction occurs when tetrafluoroboric acid is used as a catalyst to afford functionalized furans in moderate to excellent yields. A variety of alkenyl- and alkynyltrifluoroborate salts readily participate in this transformation. Full article
(This article belongs to the Special Issue Metal-free Organocatalysis)
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4 pages, 165 KiB  
Short Note
Potassium {4-[(3S,6S,9S)-3,6-dibenzyl-9-isopropyl-4,7,10-trioxo-11–oxa-2,5,8-triazadodecyl]phenyl}trifluoroborate
by Chia-Hua Tsai, Chia-Hung Lin, Ching-Tien Hsieh, Chih-Cheng Cai, Ting-Ju Lin, Pin-Yi Liu, Meng-Hsuan Lin, Meng-Ju Wu, Chia-Chieh Fu, Yang-Chang Wu, Fang-Rong Chang and Po-Shen Pan
Molbank 2014, 2014(2), M827; https://doi.org/10.3390/M827 - 30 May 2014
Viewed by 4418
Abstract
The reported compound 4 was synthesized and fully characterized by 1H NMR, 13C NMR, 11B NMR, 19F NMR, and high resolution mass spectrometry. Full article
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7 pages, 195 KiB  
Article
Microwave-Enhanced Cross-Coupling Reactions Involving Alkynyltrifluoroborates with Aryl Bromides
by Vitali Coltuclu, Eric Dadush, Abhijit Naravane and George W. Kabalka
Molecules 2013, 18(2), 1755-1761; https://doi.org/10.3390/molecules18021755 - 29 Jan 2013
Cited by 2 | Viewed by 4392
Abstract
Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium [...] Read more.
Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium catalyst has been developed using microwave irradiation. The microwave reactions are rapid and efficient. Full article
(This article belongs to the Special Issue Organoboron Chemistry)
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