Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• (TFE, Scheme 2B) [21]. Our group previously reported the synthesis of diaryliodonium(III) salts by combining hypervalent iodine(III) reagents with electron-rich arenes in fluoroalcohol solvents, such as TFE or 1,1,1,3,3,3-hexafluoro-2-propanol [21][22]. These solvents stabilize the cationic

• practical, direct approach for the synthesis of aryl(TMP)iodonium(III) carboxylates, utilizing readily accessible iodosoarenes or (diacetoxyiodo)arenes as starting materials in a fluoroalcohol solvent (Scheme 2C). This protocol allows for the synthesis of electron-rich, electron-poor, heterocyclic, and

Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF₃)₂CHOH]

• Takeshi Fujita,
• Noriaki Shoji,
• Nao Yoshikawa and
• Junji Ichikawa

Beilstein J. Org. Chem. 2021, 17, 396–403, doi:10.3762/bjoc.17.35

• gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes. Keywords: acid; catalyst; cyclization; fluoroalcohol; helicenes; Introduction Helicenes are a class of polycyclic aromatic hydrocarbons (PAH) that consist of ortho-fused aromatic rings arranged in a helical

• types of helicenes using a sequence of (i) Suzuki–Miyaura coupling of acetal-containing components and (ii) catalytic cycloaromatization with the aid of a cation-stabilizing fluoroalcohol, HFIP, as solvent. Particularly, helicene synthesis using tandem cyclization of bisacetals with teraryl structures

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

• Raju Cheerlavancha,
• Ahmed Ahmed,
• Yun Cheuk Leung,
• Aggie Lawer,
• Qing-Quan Liu,
• Marina Cagnes,
• Hee-Chan Jang,
• Xiang-Guo Hu and
• Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

• obtain sufficiently pure material for a meaningful α-fluorination test reaction to be performed. The low stability of β-fluoroaldehydes appeared to be a general phenomenon, and so an attempt was next made to generate such a substrate in situ via the oxidation of β-fluoroalcohol 19 (Table 1, entry 3

Kinetic evaluation of the solvolysis of isobutyl chloro- and chlorothioformate esters

• Malcolm J. D’Souza,
• Matthew J. McAneny,
• Dennis N. Kevill,
• Jin Burm Kyong and
• Song Hee Choi

Beilstein J. Org. Chem. 2011, 7, 543–552, doi:10.3762/bjoc.7.62

• bimolecular association–dissociation (addition–elimination) process was favored in the more nucleophilic solvents, while an ionization pathway was dominant in the highly ionizing solvents, including the fluoroalcohols with high fluoroalcohol content [7][8][10]. The l/m ratios for these three substrates in the