Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

• Sebastien Curpanen,
• Per Reichert,
• Gabriele Lupidi,
• Giovanni Poli,
• Julie Oble and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

• details). We also contemplated the use of alkyl iodides as electrophiles. Methylation with methyl iodide was efficient, as shown through the preparation of 28 in 61% yield from 4c. In contrast, higher alkyl iodides, such as ethyl iodide, failed to provide the alkylation product (i.e., 29) and only

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Enhancing the reactivity of 1,2-diphospholes in cycloaddition reactions

• Almaz Zagidullin,
• Vasili Miluykov,
• Elena Oshchepkova,
• Artem Tufatullin,
• Olga Kataeva and
• Oleg Sinyashin

Beilstein J. Org. Chem. 2015, 11, 169–173, doi:10.3762/bjoc.11.17

• cycloadducts, 2a–c, respectively. However the alkylation of sodium 1,2-diphospha-3,4,5-tri(p-fluorophenyl)cyclopentadienide with ethyl iodide leads to stable 1-ethyl-3,4,5-tris(p-fluorophenyl)-1,2-diphosphole (1e), which forms the [4 + 2] cycloadduct 2,3,4,4a,5,6-hexa(p-fluorophenyl)-1-ethyl-1,7,7a-triphospha

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• , 17.8 g (65 mmol) 2-(2-(2-methoxyethoxy)ethoxy)ethyl iodide and 17.5 mg (0.05 mmol) tetra-n-butylammonium iodide were added and the resulting reaction mixture was stirred at 60 °C under N2 for 6 d. The reaction was quenched by the addition of 50 mL of ethanol and stirred at rt for further 30 min. The

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• distillable phospholane 59, which was further converted with ethanol into 60. Treatment with ethyl iodide in an Arbuzov reaction provided the desired ethyl phosphonamide 28a (Scheme 9A) [1][30]. Cyclic phosphonamides derived from C2-symmetric diamines such as 28a do not have a stereogenic P-atom and therefore

Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

• Sebastian Reinelt,
• Monir Tabatabai,
• Urs Karl Fischer,
• Norbert Moszner,
• Andreas Utterodt and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1733–1740, doi:10.3762/bjoc.10.180

• the reaction sequence and yielded compound 3. The quantitative etherification of the phenolic hydroxy groups with potassium carbonate and ethyl iodide yielded the corresponding ether derivative 5. Subsequently the remaining hydroxy groups of 3 and 5 were o-alkylated in the presence of a strong base

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

•  1. The quantum yields for the reactions in both aqueous and organic media are known to be rather low, 1% < Φ < 5%, as summarized in Table 2 [28][29]. Only the addition of solvents with heavy atoms, such as ethyl iodide, leads to satisfactory quantum yields (up to 17%). This increase is accompanied

Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

• Miroslav Murár,
• Gabriela Addová and
• Andrej Boháč

Beilstein J. Org. Chem. 2013, 9, 173–179, doi:10.3762/bjoc.9.20

• in the presence of p-TsOH. Reduction of sulfonyl chloride E to sodium sulfinate F by Na2SO3 and Na2CO3 and its reaction with ethyl iodide proceeded as nonselective reactions, which excluded this methodology from further efforts (Scheme 1). These findings suggested that the free amine in B was

Ru-catalyzed dehydrogenative coupling of carboxylic acids and silanes - a new method for the preparation of silyl ester

• Guo-Bin Liu and
• Hong-Yun Zhao

Beilstein J. Org. Chem. 2008, 4, No. 27, doi:10.3762/bjoc.4.27

• with silanes. In the presence of 1 mol% Ru3(CO)12 and 4 mol% EtI, dehydrosilylation reactions in toluene afforded the corresponding silyl esters at 100 °C in good and high yields. Keywords: carboxylic acids; ethyl iodide; Ru3(CO)12; silanes; silylation; Introduction Polymers composed of

• finding that a catalytic system of dodecacarbonyltriruthenium and ethyl iodide [Ru3(CO)12/EtI] effectively promotes the dehydrogenative coupling of carboxylic acids with silanes, yielding the corresponding silyl esters selectively. The results are summarized in Scheme 1 and Table 1–Table 4