Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• assist in the deprotonation of intermediate II to produce final products 27, while K2S2O8 aids in the oxidation of the photocatalyst in the case of pyridine N-oxide. In another photoinduced reaction procedure, Murarka et al. reported the formation of aryl radicals from a tetrameric electron donor

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• displacement of the PhTe group with the PhS group afford 23. Furthermore, the photoinduced reaction of ortho-ethenylaryl isocyanides with bis(2-aminophenyl) disulfides affords tetracyclic compounds 24 in a single step. Not only alkynyl and alkenyl groups, but also heteroatom moieties such as azido and sulfide

• acid [58]. Rainier et al. reported the thiol-mediated 5-exo cyclization of o-alkynylaryl isocyanides, which successfully afforded dithiolated indoles 22 (Scheme 15) [59]. However, depending on the reaction conditions, quinoline derivatives were also produced as byproducts (vide infra). The photoinduced

• reaction of o-ethenylaryl isocyanides with disulfides in the presence of diphenyl ditelluride yields the corresponding dithiolated indole derivatives 23 (Scheme 16) [60]. Initially, the thiotelluration products via 5-exo cyclization are formed in situ. The subsequent aromatization followed by photoinduced

Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

• Dat Phuc Tran,
• Yuki Sato,
• Yuki Yamamoto,
• Shin-ichi Kawaguchi,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

• using a radical initiator such as 1,1'-azobis(cyclohexane-1-carbonitrile) (V-40) (Scheme 1a) [45] or upon photoirradiation (Scheme 1b) [38] yields vic-bis(diphenylphosphino)alkenes in good yields. Unfortunately, this photoinduced reaction of Ph2PPPh2 was not applicable to alkenes [42]. To change the

Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

• Grzegorz Mlostoń and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221

• radical intermediate 46 governs the formal [4 + 2]-cycloaddition reaction of E-1b with 3,4-di(α-styryl)furan (47, Scheme 15). The photoinduced reaction occurs via an electron-transfer (PET) process and led to the formation of the polycyclic product 48 in a stereospecific manner [52]. Similar products were

Photoinduced 1,2,3,4-tetrahydropyridine ring conversions

• Baiba Turovska,
• Henning Lund,
• Viesturs Lūsis,
• Anna Lielpētere,
• Edvards Liepiņš,
• Sergejs Beljakovs,
• Inguna Goba and
• Jānis Stradiņš

Beilstein J. Org. Chem. 2015, 11, 2166–2170, doi:10.3762/bjoc.11.234

• . Photoinduced reaction of 1 in O2 saturated CHCl3 under irradiation by intensive sunlight. Heterocycle transformations of 1 in air saturated CHCl3 solutions. Proposed mechanism of conversion of oxaziridine 4 to 5. Supporting Information Synthesis and characterization of all products, copies of 1H and 13C NMR

Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides

• Yohsuke Kobiki,
• Shin-ichi Kawaguchi,
• Takashi Ohe and
• Akiya Ogawa

Beilstein J. Org. Chem. 2013, 9, 1141–1147, doi:10.3762/bjoc.9.127

• absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method. Keywords: arylation; unsymmetrical diaryl selenide; free radical; organobismuth; photoinduced reaction; Introduction A number of organoselenium compounds are

• ). In 1999, Barton and co-workers reported that diaryl selenide was obtained by the reaction of triarylbismuthine with diphenyl diselenide under heating at high temperature (140 °C) [65], but the photoinduced reaction was not investigated. In this letter, we will report the radical reaction of diaryl

• diselenides with triarylbismuthines from the viewpoint of a photoinduced reaction in the synthesis of unsymmetrical diaryl selenides. Results and Discussion First, we investigated the photoinduced reaction of diphenyl diselenide with triphenylbismuthine. Diphenyl diselenide (1a, 0.1 mmol) and

Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide

• Lena Möller,
• Christian Hess,
• Jiří Paleček,
• Yi Su,
• Axel Haverich,
• Andreas Kirschning and
• Gerald Dräger

Beilstein J. Org. Chem. 2013, 9, 270–277, doi:10.3762/bjoc.9.33

• 2 with a methanolic solution of nitrene precursor 3, and then drying followed by UV irradiation (Hg lamp, 254 nm) initially did not lead to surface modification. The presence of F and N on the TPX membrane was not detectable by XPS analysis. The photoinduced reaction of azide 3 with cyclohexane