Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

• isobenzofuran-1-thiones 311 and 2-benzothiophene-1-thiones 314 with 2,3-dimethylbut-2-ene (215a) gave the corresponding spirothietanes 312 and 315 under photo irradiation. The spirothietanes 312 derived from 3-unsubstituted or 3-monosubstituted 1,3-dihydroisobenzofuran-1-thiones 311 were less stable and

• thietane derivatives 334 in 38–88% yields [93] (Scheme 64). In 1992, Oda’s group found that, under photo irradiation conditions N-but-3-enylthiophthalimides 335 underwent an intramolecular photo-assisted [2 + 2] cycloaddition first giving tricyclic thietanes 336, which further photochemically converted

• underwent a ring-opening reaction to afford pyrrolizinones 342. In case of N-but-3-enyl-5-thiopyrrolidin-2-one (338a, R = H) the reaction afforded the product 7-mercaptomethyl-1,2,5,6-tetrahydropyrrolizin-3-one (340) directly in 68% yield under photo irradiation. However, N-(3-methylbut-3-enyl)-5

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

• . found the direct carboxylation reaction with CO2 under photo-irradiation reaction conditions [46]. Jamison et al. also reported the synthesis of α-amino acid derivatives using amine and CO2 [47]. Iwasawa disclosed the Pd-catalyzed carboxylation of aryl halides using CO2 in the presence of an Ir photo

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• inclusion complexes were transferred into 50 mL quartz round-bottomed flasks and bubbled with nitrogen gas for 20 min with stirring before photo-irradiation. Photodimerization of the samples was carried out using a medium-pressure mercury lamp (166.5 W, Heraeus Noblelight GmbH, UVB) as a light source. After

Bromination of hydrocarbons with CBr₄, initiated by light-emitting diode irradiation

• Yuta Nishina,
• Bunsho Ohtani and
• Kotaro Kikushima

Beilstein J. Org. Chem. 2013, 9, 1663–1667, doi:10.3762/bjoc.9.190

• : bromination; free radical; hydrocarbon; light-emitting diode; photo irradiation; Introduction Bromination reactions of organic compounds are fundamental reactions for providing a wide variety of organic precursors for industrial materials [1][2][3][4][5][6][7][8]. Generally, the bromination of saturated

• activation of CBr4 is therefore considered to be induced by photo-irradiation, initiating the reaction. Although other light sources could also activate CBr4, we adopted LED light due to safety, mildness, and availability. We have confirmed that fluorescent room light could also promote the reaction. A

• plausible mechanism for the present bromination is illustrated in Scheme 1. First, photo-irradiation generates a bromine radical and a CBr3 radical (Scheme 1, reaction 1), which abstracts a hydrogen atom from the substrate to form CHBr3 (Scheme 1, reaction 2). Finally, the radical species derived from the

Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones

• Yingdong Luo,
• Guozhu Zhang,
• Erik S. Hwang,
• Thomas A. Wilcoxon and
• Liming Zhang

Beilstein J. Org. Chem. 2011, 7, 596–600, doi:10.3762/bjoc.7.69

• of note that α-methanesulfonyloxy ketones are versatile synthetic intermediates that can undergo various reactions [27], including substitution [28], elimination [29], the formation of zinc homoenolates [30], the formation of cyclopropane rings under photo-irradiation [31][32][33], the formation of