Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

• Yukiko Karuo,
• Keita Hirata,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

• cyclopropylboronic acid (4n) achieved to give 2n in a 71% yield (Table 3, entry 13). When thiopheneboronic acid 4o was used as a coupling partner, the thiophene ring could be installed on 1a in a comparatively low yield of 31% (Table 3, entry 14). In addition, we investigated the substrate scope of 1 in the Suzuki

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

• Nicky J. Willis,
• Elliott D. Bayle,
• George Papageorgiou,
• David Steadman,
• Benjamin N. Atkinson,
• William Mahy and
• Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

• efficient step in our sequence and justified further optimisation (vide infra). Suzuki–Miyaura cross coupling of bromide 5 with cyclopropylboronic acid (2.5 equiv) produced 6 in good yield (62–89%) but the product required extensive chromatographic purification. We reasoned that switching from the boronic

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

• Emeline Benoit,
• Ahmed Fnaiche and
• Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

• Emeline Benoit Ahmed Fnaiche Alexandre Gagnon Département de chimie, Université du Québec à Montréal, C.P. 8888, Succursale Centre-Ville, Montréal, Québec, H3C 3P8, Canada 10.3762/bjoc.15.113 Abstract The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported

• thiophenol was also accomplished using potassium cyclopropyl trifluoroborate. Keywords: aryl cyclopropyl sulfides; copper(II) acetate; copper catalysis; cyclopropylboronic acid; thiophenols; Introduction Aryl cyclopropyl sulfides are present in many biologically active compounds, mainly in their oxidized

• tricyclopropylbismuth (24) which transfers only one cyclopropyl unit out of three to deliver the desired products in moderate yields. Cyclopropylboronic acid has been elegantly used by Neuville and Zhu [39][40], Tsuritani [41], Taillefer [42], Hayashi [43] and Reddy [44] as a cyclopropylating reagent in N

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

• Eloi P. Coutant,
• Vincent Hervin,
• Glwadys Gagnot,
• Candice Ford,
• Racha Baatallah and
• Yves L. Janin

Beilstein J. Org. Chem. 2018, 14, 2853–2860, doi:10.3762/bjoc.14.264

• derivative 29. Indeed, coupling these compounds with cyclopropylboronic acid gave the corresponding cyclopropyl derivatives 14, 18 or 30 in 60, 47 and 75% yield, respectively. The palladium-based reduction of compound 14 and 18 also led to the hydrogenation of their cyclopropyl ring into a propyl side chain