Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

• Zhensheng Zhao and
• Graham K. Murphy

Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

• vicinal-dichlorination of phenylallenes; however, no such chlorination reaction has yet been achieved [29][30][31][32][33][34]. Recent reports of reactions between hypervalent iodine reagents and phenylallenes have highlighted the possible product outcomes achievable through ionic and radical reaction

• a 1,2-phenyl shift (C to D, Scheme 1c). There has been no investigation of the chemistry between arylallenes and chlorinated hypervalent iodine reagents, and given the differing reactivities that might be achievable with (dichloroiodo)benzene [40] (1a) and chlorobenziodoxolone (1b) [30][41][42][43

Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)

• Morifumi Fujita,
• Koki Miura and
• Takashi Sugimura

Beilstein J. Org. Chem. 2018, 14, 659–663, doi:10.3762/bjoc.14.53

• the electronic and steric properties of the aryl group and the heteroatomic ligand coordinated to the iodine atom. Optically active hypervalent iodine compounds contain chiral ligands or chiral aryl groups. Several types of optically active hypervalent iodine reagents and catalysts have been developed

• . [15][16][17] reported the dioxytosylation of styrene (1a, Scheme 1). Chiral hypervalent iodine reagents 2 bearing a 1-methoxyethyl side chain were used for enantiocontrol of the dioxytosylation, and the maximum enantiomeric excess (ee) of the product 3a reached 65%. Despite recent rapid progress in

• the field of asymmetric oxidation achieved by chiral hypervalent iodine compounds, there has been no subsequent examination of dioxytosylation, which can be used as a standard reaction for comparing the enantiocontrolling ability of chiral hypervalent iodine reagents. The design of chiral hypervalent

Synthesis of fluoro-functionalized diaryl-λ³-iodonium salts and their cytotoxicity against human lymphoma U937 cells

• Prajwalita Das,
• Etsuko Tokunaga,
• Hidehiko Akiyama,
• Hiroki Doi,
• Norimichi Saito and
• Norio Shibata

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

• developed, including Shibata reagents I [20] and II [21] (trifluoromethylation reagent 1 and trifluoromethylthiolation reagent 2a, respectively), pentafluorophenylating reagent 2b and several hypervalent iodine reagents, i.e., diaryliodonium salts with a mesitylene ligand (3a–o) and a triisopropylphenyl

Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

• Hao Wang,
• Cui Chen,
• Weibing Liu and
• Zhibo Zhu

Beilstein J. Org. Chem. 2017, 13, 2023–2027, doi:10.3762/bjoc.13.200

• light [19][20], hypervalent iodine reagents [21][22], acids [23], organoammonium iodides [24] and iodine [25]. These catalysts are often employed in combination with a peroxide and generally produce an organoperoxide. Organic peroxides are important and useful compounds because of their unique chemical

Iodoarene-catalyzed cyclizations of N-propargylamides and β-amidoketones: synthesis of 2-oxazolines

• Somaia Kamouka and
• Wesley J. Moran

Beilstein J. Org. Chem. 2017, 13, 1823–1827, doi:10.3762/bjoc.13.177

• cyclization of N-propargylamides and the second involves the cyclization of β-amidoketones. These are proposed to proceed through different mechanisms and have different substrate scopes. Keywords: amides; catalysis; cyclization; hypervalent iodine; isoxazolines; Introduction Hypervalent iodine reagents are

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• hypervalent iodine reagents [9][10][11][12], and homogeneously or heterogeneously catalyzed multicomponent reactions [13][14]. Moreover, radical cyclizations predominantly conducted using Bu3SnH in the presence of azobisisobutyronitrile (AIBN) play a crucial role [15][16]. However, all these methods require

IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives

• Caifei Tang,
• Zhiming Li and
• Quanrui Wang

Beilstein J. Org. Chem. 2013, 9, 2629–2634, doi:10.3762/bjoc.9.298

• aldehydes, affording the corresponding hydrazones 4. In general, aromatic aldehydes provided higher yields than aliphatic aldehydes. In recent years, organo hypervalent iodine reagents have drawn considerable interests as versatile and environmentally benign oxidants with many applications in organic

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

• ”, and balancing the electron transfer to the perfluoroalkyl iodide. In 2010, A. Togni and coworkers studied the trifluoromethylation of pyrroles, indoles, and various other heteroarenes or arenes in the presence of zinc salts, and with Togni’s hypervalent iodine reagents as the CF3-source. Yields were

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

• Raoni S. B. Gonçalves,
• Michael Dos Santos,
• Guillaume Bernadat,
• Danièle Bonnet-Delpon and
• Benoit Crousse

Beilstein J. Org. Chem. 2013, 9, 2387–2394, doi:10.3762/bjoc.9.275

• available reagents have been employed under metal-free conditions. A group [27] reported that the hypervalent iodine reagents (diacetoxyiodo)benzene (DIB) and phenyliodine bis(trifluoroacetate) (PIFA) could successfully promote the oxidation of aldoximes to the corresponding nitrile oxide. Those reagents

Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans

• Yifan Li and
• Jérôme Waser

Beilstein J. Org. Chem. 2013, 9, 1763–1767, doi:10.3762/bjoc.9.204

• the use of ethynylbenziodoxolones, which are cyclic hypervalent iodine reagents [22][23]. Nevertheless, the conditions we have used for other heterocycles gave only very low yields in the case of benzofurans. Herein, we would like to report the first catalytic direct C2-alkynylation of benzofurans 7

Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation

• Nida Ambreen,
• Ravi Kumar and
• Thomas Wirth

Beilstein J. Org. Chem. 2013, 9, 1437–1442, doi:10.3762/bjoc.9.162

• –Doering oxidation [3]. In synthetic chemistry, selective methods for the oxidation of alcohols are highly sought after, and methods with the ability to differentiate between various functional groups are desired. The use of hypervalent iodine reagents in organic chemistry has increased during recent years

• . Enhanced mass- and heat transfer and short diffusion distances can lead to better yields within shorter reaction times [15]. Herein, we describe the development of continuous-flow systems using hypervalent iodine reagents in the TEMPO-mediated oxidation of alcohols with the advantage of significantly

Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides

• Wei-Bing Liu,
• Cui Chen,
• Qing Zhang and
• Zhi-Bo Zhu

Beilstein J. Org. Chem. 2012, 8, 344–348, doi:10.3762/bjoc.8.38

• chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides. Keywords: cleavage of carbon–carbon bond; (diacetoxyiodo)benzene; difunctionalized acetamides; novel oxidation

Dioxane dibromide mediated bromination of substituted coumarins under solvent-free conditions

• Subrata Kumar Chaudhuri,
• Sanchita Roy and
• Sanjay Bhar

Beilstein J. Org. Chem. 2012, 8, 323–329, doi:10.3762/bjoc.8.35

• [8], Et4N+Br− in the presence of hypervalent iodine reagents [9], and NBS in tetrabutylammonium bromide under molten salt conditions [10]. There is a recent report of the preparation of 3-bromocoumarins from acyclic precursors through bromination of a Wittig reagent with NBS followed by tandem Wittig

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

• Jonathan P. Brand,
• Clara Chevalley and
• Jérôme Waser

Beilstein J. Org. Chem. 2011, 7, 565–569, doi:10.3762/bjoc.7.65

• heterocycles has been intensively investigated [30][31][32][33][34]. Most of the developed methods involve the use of haloacetylenes. In contrast, our group has focused on the use of more reactive alkynyl hypervalent iodine reagents in order to expand the scope of direct alkynylation methods under milder

m-Iodosylbenzoic acid – a convenient recyclable reagent for highly efficient aromatic iodinations

• Andreas Kirschning,
• Mekhman S. Yusubov,
• Roza Y. Yusubova,
• Ki-Whan Chi and
• Joo Y. Park

Beilstein J. Org. Chem. 2007, 3, No. 19, doi:10.1186/1860-5397-3-19

• recycling of the iodine reagent is concerned. The broad use of hypervalent iodine reagents is still hampered by tedious purification and recycling protocols. Commonly, purification relies on chromatography. Recently, tagging strategies for reagents and catalysts have widely been investigated that allow easy

• but could potentially be applied to most other iodine(III)-mediated reactions. Hypervalent iodine reagents 1 – 6. Iodine(III)-promoted iodination of arenes and concept of purification. Proposed intermediates. Monoiodination of arenes with m-iodosylbenzoic acid 6 (see Supporting Information File 1 for