Visible-Light-Promoted Selenofunctionalization of Alkenes

Abstract

A visible-light-promoted method for the selenofunctionalization (and tellurofunctionalization) of alkenes has been developed. This method obviates the prepreparation of moisture-sensitive chalcogen electrophiles. The experimental setup is simple, and superior yields are obtained in the case of selenofunctionalization (up to 99%) while moderate to good yields are obtained in the case of tellurofunctionalization (53-75%). A variety of intra- and intermolecular processes and a short synthesis of the Amaryllidaceae alkaloid (±)-γ-lycorane are demonstrated with this method.

Visible‐Light‐Induced Hydroxysulfurization and Alkoxysulfurization of Styrenes in the Absence of Photocatalyst: Synthesis of β‐Hydroxysulfides and β‐Alkoxysulfides

“…Note that we accomplished this reaction without a photocatalyst or a strong oxidant. Meanwhile, ArSSAr/CBr 4 reaction system was first used as a universal platform for hydroxysulfurization and alkoxysulfurization of styrenes; however, no literature has reported the use of diol as a substrate for the preparation of β‐alkoxysulfide (Scheme f) . In this study, we report this photochemical difunctionalization for the preparation of β‐oxy sulfides in the absence of a photocatalyst and an oxidant.…”

“…Meanwhile, ArSSAr/CBr 4 reaction system was first used as a universal platform for hydroxysulfurization and alkoxysulfurization of styrenes; however, no literature has reported the use of diol as a substrate for the preparation of β-alkoxysulfide (Scheme 1f). [13] In this study, we report this photochemical difunctionalization for the preparation of β-oxy sulfides in the absence of a photocatalyst and an oxidant. This greener hydroxysulfurization and alkoxysulfurization of styrenes has shown high efficiency and regioselectivity.…”

“…Further solvent screening indicated that acetone, DCE, and THF gave comparable product yields (Table 1, entries 10-12). Additionally, we obtained moderate yields (52-68%) when we used dimethylformamide (DMF), ethyl acetate (EtOAc), toluene, and H 2 O as the reaction media (Table 1, entries[13][14][15][16][17]. Notably, we also produced the desired Selected examples for the synthesis of β-oxy sulfides from alkenes.…”

Automated Electrochemical Selenenylations

“…The spectral data are in agreement with the literature. 20 1 H NMR (500 MHz, CDCl 3 ):  = 7.62-7.46 (m, 2 H), 7.33-7.26 (m, 3 H), 4.69-4.61 (m, 1 H), 3.29 (dd, J = 12.9, 4.8 Hz, 1 H), 3.01 (dd, J = 12.9, 8.0 Hz, 1 H), 2.62-2.36 (m, 3 H), 2.00-1.90 (m, 1 H).…”

Hydroamination of Dihapto‐Coordinated Benzene and Diene Complexes of Tungsten: Fundamental Studies and the Synthesis of γ‐Lycorane

“…The first asymmetric synthesis of γ‐lycorane was reported by Mori in 1995, [23] and its structure is considered prototypical for this important class of alkaloids. In just the past five years, well over a dozen new syntheses of the lycorine family have appeared [24–37] . Of these, only one uses a benzene ring as the source of the C ring, which contains all of the stereocenters.…”