Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

• Javier Ajenjo,
• Martin Greenhall,
• Camillo Zarantonello and
• Petr Beier

Beilstein J. Org. Chem. 2016, 12, 192–197, doi:10.3762/bjoc.12.21

• nitrogen nucleophiles provided 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzenes substituted in position four. Keywords: direct fluorination; fluorine; nucleophilic aromatic substitution; pentafluorosulfanyl group; vicarious nucleophilic substitution; Introduction Organic compounds with a

Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

• Norbert Vida,
• Jiří Václavík and
• Petr Beier

Beilstein J. Org. Chem. 2016, 12, 110–116, doi:10.3762/bjoc.12.12

• : dearomatization; decarboxylation; Diels–Alder reaction; oxidation; pentafluorosulfanyl group; Introduction Fluorinated organic compounds have been one of the foci of chemical industry for the last several decades. The unique properties of fluorine atoms and fluorinated groups have been exploited in various

Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines

• Alexander Penger,
• Cortney N. von Hahmann,
• Alexander S. Filatov and
• John T. Welch

Beilstein J. Org. Chem. 2013, 9, 2675–2680, doi:10.3762/bjoc.9.303

• consistent with retardation the rate of E/Z imine isomerization by the electron withdrawing pentafluorosulfanyl group [35]. In the reaction of 12, the E/Z ratio of the imine was reflected very well in the 1,2-diastereomeric excess of the product β-lactam 7e . The ketene–imine condensation of 7c is influenced

• by the presence of the pentafluorosulfanyl group at a stereogenic center. The 1,2-lk,lk (Si,Si-S) (or (Re,Re-R)) stereochemistry of 7c (Figure 2) suggests the profound dipole associated with the introduction of the SF5 group may influence the diastereoselectivity of ring closure. The initial approach

• of the ketene (A in Scheme 4) appears to be influenced by avoidance of unfavorable interaction of the ketene with the sterically demanding SF5 group. Previously it was found in single crystal X-ray diffraction studies that the pentafluorosulfanyl group [48] is predictably orthogonal to a carbonyl

Synthesis of SF₅-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes

• Petr Beier and
• Tereza Pastýříková

Beilstein J. Org. Chem. 2013, 9, 411–416, doi:10.3762/bjoc.9.43

• yields. Their synthetic utility was demonstrated by condensation reactions with carbonyl compounds or amines to provide SF5-containing quinolines and quinazolines, respectively. Keywords: benzisoxazoles; pentafluorosulfanyl group; quinazolines; quinolines; sulfurpentafluorides; Introduction Reactions

Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction

• George Iakobson and
• Petr Beier

Beilstein J. Org. Chem. 2012, 8, 1185–1190, doi:10.3762/bjoc.8.131

• good yields and high stereoselectivities. Follow-up transformations of the primary products provided (E)-1-alkenyl-(pentafluorosulfanyl)benzenes and 2-(2-arylethyl)-(pentafluorosulfanyl)anilines. Keywords: Horner–Wadsworth–Emmons reaction; pentafluorosulfanyl group; phosphonates; sulfurpentafluoride