Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

• Carlos R. Azpilcueta-Nicolas and
• Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

• reported notable examples of these transformations, involving the Zn0-mediated cross-coupling of redox-active esters with chlorophosphines [102] and gem-difluoroalkenes [103], respectively. In the report by Sun and co-workers, it was proposed that the activation of RAE 10 occurs upon reduction with Zn

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

• Tzu-Yu Huang,
• Mario Djugovski,
• Sweta Adhikari,
• Destinee L. Manning and
• Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

• gem-difluoroalkenes with organic azides in morpholine as a solvent to construct fully decorated morpholine-substituted 1,2,3-triazoles. Mechanistic studies revealed the formation of an addition–elimination intermediate of morpholine and gem-difluoroalkenes prior to the triazolization reaction via two

• ; gem-difluoroalkenes; organic azides; Introduction gem-Difluoroalkenes and their synthetic preparations soared in the last decade, driven by the high demand for carbonyl mimics in medicinal chemistry and drug discovery [1]. Although a wide array of functionalization strategies for gem-difluoroalkenes

• cycloaddition or addition–elimination reactions with 1,3-dipoles and gem-difluoroalkenes is largely unexplored and the only report of a cycloaddition is with 2-fluoroindolizines (Figure 1A) via a β-fluoride elimination in an SNV (nucleophilic vinylic substitution)-like transformation [9]. Nucleophilic addition

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

• Fei Wang,
• Lingchun Li,
• Chuanfa Ni and
• Jinbo Hu

Beilstein J. Org. Chem. 2014, 10, 344–351, doi:10.3762/bjoc.10.32

• failure of the current reaction. Using the conditions shown in Table 1, entry 2 as standard, the olefination of aldehydes with TMSCF2Cl was investigated. As shown in Figure 1, a variety of structurally diverse aromatic aldehydes were successfully converted into gem-difluoroalkenes 2a–g in moderate to good

Flow microreactor synthesis in organo-fluorine chemistry

• Hideki Amii,
• Aiichiro Nagaki and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2013, 9, 2793–2802, doi:10.3762/bjoc.9.314

• using microreactor systems. Use of DAST in continuous-flow reactors. Flow microreactor synthesis of fluorinated epoxides. Highly controlled isomerization of gem-difluoroalkenes. Flow system for catalytic aromatic fluorination. Continuous-flow reactor for electrophilic aromatic fluorination. Examples of