Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

• Shyam Sathyamoorthi,
• Appasaheb K. Nirpal,
• Dnyaneshwar A. Gorve and
• Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

• ring was opened in a diastereoselective (SN2 type) and exo-selective manner by a trifluoroacetate anion. The trifluoroacetate anion was conveniently derived from (bis(trifluoroacetoxy)iodo)benzene (PIFA), which was used as the stoichiometric oxidant in the reaction. Overall, this amounted to a highly

Divergent role of PIDA and PIFA in the AlX₃ (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study

• Kevin A. Juárez-Ornelas,
• Manuel Solís-Hernández,
• Pedro Navarro-Santos,
• J. Oscar C. Jiménez-Halla and
• César R. Solorio-Alvarado

Beilstein J. Org. Chem. 2024, 20, 1580–1589, doi:10.3762/bjoc.20.141

• , Br) [26][27][28][29][30][31]. So far, different protocols for the halogenation of arenes using iodine(III) reagents have been described, mainly using (diacetoxyiodo)benzene (PIDA)/TMSCl, PIDA/TMSBr [32], and [bis(trifluoroacetoxy)iodo]benzene (PIFA)/TMSBr [33]. We have recently developed a new

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• of natural product-like compound libraries. Keywords: [bis(trifluoroacetoxy)iodo]benzene PIFA; nitrogen heterocycles; oxidative cyclization; pyrrolo[1,2-a]quinazolines; Introduction An important design concept in current drug discovery includes structural modifications of naturally occurring

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• (trifluoroacetoxy)iodo]benzene] (PIFA) and BF3·OEt2 in dichloromethane at −78 °C afforded, after 12 h, the desired cyclized product 8a in 59% yield. The reaction could be performed on a 0.5 mmol scale in a similar yield of 58%. Note that other typical reagents used for the Scholl reaction, such as DDQ/CF3CO2H

• furnished the phosphole-fused ortho-teraryl products 7a–c in moderate to high yields. With the phosphole-fused ortho-teraryl compounds 7 in hand, we next examined their cyclization into triphenylene derivatives by the Scholl reaction (Scheme 3) [30]. The reaction of 7a (0.1 mmol) in the presence of [bis

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

• Fateh V. Singh,
• Priyanka B. Kole,
• Saeesh R. Mangaonkar and
• Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

• β-substituted 3-(methoxyphenyl)-N-methoxypropionamides 46 with [bis(trifluoroacetoxy)iodo]benzene (PIFA, 31) in dichloromethane (Scheme 14). The reactions were carried out at low temperature and spirolactams 47 were achieved in high yields with up to 96% enantiomeric excess. Furthermore, these

Iodine(III)-mediated halogenations of acyclic monoterpenoids

• Laure Peilleron,
• Tatyana D. Grayfer,
• Joëlle Dubois,
• Robert H. Dodd and
• Kevin Cariou

Beilstein J. Org. Chem. 2018, 14, 1103–1111, doi:10.3762/bjoc.14.96

• )iodobenzene (DIB) and lithium bromide yield a dibromo adduct (Scheme 1, reaction 2), whereas a combination of (bis(trifluoroacetoxy)iodo)benzene (PIFA) and tetra-n-butylammonium bromide (TBAB) gives bromo(trifluoro)acetoxylated 3a (Scheme 1, reaction 3) [16]. We then decided to further explore the synthetic

Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

• Lynnie Trzoss,
• Jing Xu,
• Michelle H. Lacoske and
• Emmanuel A. Theodorakis

Beilstein J. Org. Chem. 2013, 9, 1135–1140, doi:10.3762/bjoc.9.126

• ) reductive deoxygenation with LiEt3BH (super hydride). The thioketal protecting group was then removed under oxidative conditions with [bis(trifluoroacetoxy)iodo]benzene (PIFA) to yield ketone 10 in good yield (66% over three steps, Scheme 2) [78]. This approach allowed us to produce a sufficient amount of