Palladium-Catalyzed Markovnikov-Selective Hydroselenation of N-Vinyl Lactams with Selenols Affording N,Se-Acetals

Tamai, Toshiyuki; Yoshikawa, Megumi; Higashimae, Shinya; Nomoto, Akihiro

doi:10.1021/acs.joc.5b02431

Cited by 15 publications

(11 citation statements)

References 40 publications

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“…A highly selective palladium(II) diacetate catalyzed hydroselenation of N ‐vinyl lactams to yield N , Se ‐acetals of formula 45 has been depicted [87] . If the vinyl moiety in 46 is unsubstituted (R=H) the molecule is able to afford the Markovnikov‐type adduct but if R is not a hydrogen atom, a palladium catalyst is required for the reaction to occur [87] .…”

Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium‐containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium‐containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

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Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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“…The complex 82 is stabilised by coordination of heteroatoms to the palladium atom. Regioselective selenopalladation affords the intermediate 83 , which undergoes protonation with the selenol providing the Markovnikov‐type adduct 79 and regenerating the palladium‐selenide complex 81 (Scheme 39, part b ) [89] …”

Section: Synthetic Applications Of Selenolsmentioning

confidence: 99%

“…Regioselective selenopalladation affords the intermediate 83, which undergoes protonation with the selenol providing the Markovnikov-type adduct 79 and regenerating the palladium-selenide complex 81 (Scheme 39, part b). [89] Besides their versatility in carbon-selenium bond forming reactions, selenols also behave as convenient reagents for the formation of selenium-heteroatom bonds. In this context, compounds bearing a seleniumsulfur bond (i. e. selenenyl sulfides) [90] are particularly important in biology.…”

Section: Synthesis Of Selenium-containing Small Moleculesmentioning

confidence: 99%

Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium-containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium -and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety -is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. Conclusions and Outlook 5.1. Safety Measures

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“…Compared to thiols, selenols have a lower p K a (the p K a s of benzeneselenol and thiophenol are 5.9 and 6.6, respectively) and weaker X–H bonds (67–74 and 78 kcal/mol, respectively) . Selenols are known to readily add into Michael acceptors, including α,β-unsaturated ketones, a vinylsulfonamide, nitroalkenes, and N -vinyl lactams . There has also been difunctionalization of alkenes to form selenides emerging; however, enantioselective variants of this approach remain unknown .…”

mentioning

confidence: 99%