3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes

Yang, Yudong; Xu, Lu; Tokunaga, Etsuko; Shibata, Norio

doi:10.1016/j.jfluchem.2012.06.007

Cited by 21 publications

(16 citation statements)

References 41 publications

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“…The unique combination of properties the SF 5 group imparts includes high chemical, thermal, and metabolic stability, strong electron-acceptor property, and high lipophilicity. Furthermore, applications of SF 5 compounds in catalysis [ 31 – 32 ], life-science [ 6 , 18 , 33 – 38 ], and material sciences [ 5 , 19 , 38 – 39 ] are emerging.…”

Section: Introductionmentioning

confidence: 99%

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

Iakobson¹,

Du²,

Slawin³

et al. 2015

Beilstein J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

Iakobson¹,

Du²,

Slawin³

et al. 2015

Beilstein J. Org. Chem.

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“…6c, 7 Moreover, a large number of 1,3‐dichloro‐aromatics are frequently encountered in parts of structures of biologically active compounds, in particular, agrochemicals, the 1,3‐bis(pentafluorosulfanyl)aromatics are highly likely to have unique biological activity due to the structural similarity. Recently, we reported the preparation of (3,5‐bis(pentafluoro‐ λ 6 ‐sulfanyl)phenyl)boronic acid ( 1 ) and its utility as an organocatalyst 5h. A boronic acid should also be attractive as a pentafluorosulfanyl‐aromatic building block under the Suzuki–Miyaura coupling reaction 8.…”

Section: Methodsmentioning

confidence: 99%

Bis(pentafluorosulfanyl)phenyl Azide as an Expeditious Tool for Click Chemistry toward Antitumor Pharmaceuticals

et al. 2014

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The inclusion of fluorine in pharmaceutical agents is a well- established means of improving their druglike properties. Different substituents have been used to introduce fluorine, including trifluoromethyl and trifluoromethylthio groups; however, the pentafluorosulfanyl remains relatively underutilized although it is considered to be a "super" trifluoromethyl group. Here, a series of pentafluorosulfanyl-containing 1,4-disubstituted-1,2,3-triazoles were synthesized by click reaction from alkynes and 3,5-bis(pentafluorosulfanyl)phenyl azide in excellent yields. Their biological activities were evaluated against human leukemic monocyte lymphoma U937 cells. In particular, 1-(3,5-bis(pentafluorosulfanyl)phenyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole exhibited potent efficacy in cell viability assays at a concentration of 60 μM and was shown to activate caspase-3 activity, indicating induction of apoptosis. An analogous fluorenol-substituted triazole also exhibited promising cytotoxic effects against U937 cells, with an IC50 value of 6.29 μM. Given these preliminary results, these pentafluorosulfanyl-containing triazoles represent useful building blocks for the further development of novel antitumor agents.

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“…Aryl bromide 3w has been widely used for the introduction of a3 ,5-bis(pentafluorosulfanyl)phenyl moietyi nt he synthesis of Pd complexes, [27] in medicinal chemistry, [28] in dye synthesis, [29] and in catalystdesign. [30] Translating the fluorination from batch setup to af low process mightl ead to increased yields and better selectivity. To wardt his goal, fluorination of 1b in flow was investigated.…”

Section: Synthesismentioning

confidence: 99%

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

Ajenjo

Klepetářová

Greenhall³

et al. 2019

Chemistry A European J

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Direct fluorination of ortho-, meta-a nd para-substituteda romatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF 5 -containing building blocks. Fluorinationsi nb atch and flow modes were compared.Acomprehensive computational study was carried out employingd ensity functional and wave functionm ethods to elucidate the reaction mechanism of the transformation of ArSF 3 into ArSF 5 .E liminating various nonradical pathways, it has been shown that the reaction proceedsb yaradical mechanism,i nitiated by the attack of the FC on the ArSF 3 moiety,p ropagated via an almostb arrierless F 2 + ArSF 4 C!ArSF 5 + FC step and terminated by the ArSF 4 C + FC!ArSF 5 .M ost of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.

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3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes

Cited by 21 publications

References 41 publications

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

Bis(pentafluorosulfanyl)phenyl Azide as an Expeditious Tool for Click Chemistry toward Antitumor Pharmaceuticals

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

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3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes

Cited by 21 publications

References 41 publications

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

Bis(pentafluorosulfanyl)phenyl Azide as an Expeditious Tool for Click Chemistry toward Antitumor Pharmaceuticals

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

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Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes