Simple and convenient synthesis of fluoroalkenes via direct coupling of alcohols, alkynes and fluoroboric acid under metal-free conditions

Yan, Xiao‐Wei; Zhang, Qiang; Wei, Wei; Ji, Jian‐Xin

doi:10.1016/j.tetlet.2014.05.069

Cited by 15 publications

(12 citation statements)

References 44 publications

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“…In 2014, Zhang, Ji, and co-workers developed the direct coupling of alcohols, alkynes, and tetrafluoroboric acid under metalfree conditions. 105 The coupling was performed with diarylmethanols and terminal alkynes to afford monofluoroalkenes with a slight selectivity for the E-alkenes (Scheme 89). The proposed mechanism is as follows: the alcohol is first activated by a proton to generate the corresponding carbocation.…”

Section: Carbofluorinationmentioning

confidence: 99%

“…In 2014, Zhang, Ji, and co-workers utilized the ability of alcohols to act as carbon-centered electrophiles in a new reaction where alkynes, diarylmethanols, and tetrafluoroboric acid were directly coupled to form fluoroalkenes, usually with moderate to good E selectivity ( Table 17). 105 In this transformation, tetrafluoroboric acid served both as an acid…”

Section: Carbofluorinationmentioning

confidence: 99%

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Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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Section: Carbofluorinationmentioning

confidence: 99%

Section: Carbofluorinationmentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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“…Ji and coworkers applied a similar strategy on the intermolecular coupling between alcohol and alkyne to synthesize monofluoroalkene 58 (Fig. 23) [43]. However, this…”

Section: Fluorination Of Alkyne To Prepare Difunctionalized Alkenyl Fmentioning

confidence: 99%

Functionalization of Alkynes for Preparing Alkenyl Fluorides

Liang¹,

Hammond²,

Xu³

2017

Fluorination

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“…9 The structural arrangement of these alcohols eases the activation of the C-O bond, as the positively charged intermediates are stabilised by the π-electron cloud through resonance. 9 Those substrates are now commonly used as sources of "proto-electrophiles" for substitution reactions, and various catalytic methodologies have been developed for the formation of C-C, 10,11 C-N, [12][13][14] C-O, [15][16][17][18][19][20][21] and C-S 22 bonds (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%