Iron-Catalyzed Transfer Hydrogenation of Allylic Alcohols with Isopropanol Md Abdul Bari, Salma A. Elsherbeni, Tahir Maqbool, Daniel E. Latham, Edward B. Gushlow, et al. Journal of Organic Chemistry, 2024 Herein, we report an iron-catalyzed transfer hydrogenation of allylic alcohols. The operationally simple protocol employs a well-defined bench stable (cyclopentadienone)iron(0) carbonyl complex as a precatalyst in combination with K2CO3 (4 mol %) and isopropanol as the hydrogen donor. A diverse range of allylic alcohols undergo transfer hydrogenation to form the corresponding alcohols in good yields (33 examples, ≤83% isolated yield). The scope and limitations of the method have been investigated, and experiments that shed light on the reaction mechanism have been conducted.
Accessing Highly Substituted Indoles via B(C6F5)3-Catalyzed Secondary Alkyl Group Transfer Salma A. Elsherbeni, Rebecca L. Melen, Alexander P. Pulis, Louis C. Morrill Journal of Organic Chemistry, 2024 Herein, we report a synthetic method to access a range of highly substituted indoles via the B(C6F5)3-catalyzed transfer of 2° alkyl groups from amines. The transition-metal-free catalytic approach has been demonstrated across a broad range of indoles and amine 2° alkyl donors, including various substituents on both reacting components, to access useful C(3)-alkylated indole products. The alkyl transfer process can be performed using Schlenk line techniques in combination with commercially available B(C6F5)3·nH2O and solvents, which obviates the requirement for specialized equipment (e.g., glovebox).
Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction Rebecca L. Melen, Louis C. Morrill, Alexander P. Pulis, Joseph P. Gillions, Salma A. Elsherbeni, et al. Synlett, 2023 C–H functionalization is widely regarded as an important area in the development of synthetic methodology, enabling the design of more time- and atom-efficient syntheses. The ability of electron-deficient organoboranes to mediate hydride abstraction from α-amino C–H bonds is therefore of great interest, as the reactive iminium and hydridoborate moieties generated are able to participate in a range of synthetically useful transformations. In this review, we cover the recent advances made in organoborane-mediated hydride abstraction, and focus on the catalytic applications of electron-deficient boranes in α- or β-functionalization, α,β-difunctionalization, and the dehydrogenation of amines.1 Introduction2 α-Functionalization of Amines3 β-Functionalization of Amines4 α,β-Difunctionalization of Amines5 Dehydrogenation of Amines6 Summary and Future Prospects
B(C6F5)3-Catalyzed E-Selective Isomerization of Alkenes Betty A. Kustiana, Salma A. Elsherbeni, Thomas G. Linford‐Wood, Rebecca L. Melen, Matthew N. Grayson, et al. Chemistry A European Journal, 2022 Herein, we report the B(C6F5)3‐catalyzed E‐selective isomerization of alkenes. The transition‐metal‐free method is applicable across a diverse array of readily accessible substrates, giving access to a broad range of synthetically useful products containing versatile stereodefined internal alkenes. The reaction mechanism was investigated by using synthetic and computational methods.
