The decarboxylation of free carboxylic acids was effected by a photogenerated cation radical phenanthrene to yield the reduction product in presence thiol, which provides an alternative method Barton procedure for aliphatic such as N-Boc amino acids.

Inter- and intramolecular additions of alkyl radicals, generated by SET photochemical decarboxylation reactions free carboxylic acids, to electron-deficient alkenes take place under mild conditions as part efficient routes for the formation N-Boc γ-amino acids macrocyclic lactones.

Photoinduced reactions of arylboronic acids with electron deficient alkenes under mild organic photoredox catalysis conditions lead to the formation Meerwein arylation type adducts via generation aryl radicals.

Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions mild heating afforded adducts, arylboronate esters, the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted generation aryl radicals via decarboxylation. A diverse range were found be suitable substrates for this photoreaction. Only our two-molecule system can work well...

The detailed mechanism of photoinduced decarboxylative radical addition to alkenes using both the effect an electron donor (ED)/electron acceptor (EA) and laser flash photolysis in a two-molecule photoredox system was investigated. concentration EA•- played important role photoreaction could be controlled by varying concentrations ED/EA their identity, which influenced ΔGPET. Higher larger negative ΔGPET led higher EA•-, thereby increasing yield adduct; however, large for generation EDA...

Deuterium exchange of a carboxy group was achieved by photochemical decarboxylation free carboxylic acids in the presence thiol and small amount D2O, deuterated product with excellent deuterium content obtained; this reaction is practical means synthesizing regioselective deuterium-labelled compounds under mild conditions.

A new method for the synthesis of macrocyclic lactones, lactams, and ketones, which utilizes photoinduced intramolecular radical cyclization reactions substrates containing tethered carboxylic acids α,β-unsaturated carbonyl moieties, has been uncovered. Photocyclization acrylate ester, were prepared starting from gave two-carbon elongated lactones via decarboxylation. Similar photoreactions acid acryl amide or ketone also produced lactams respectively. The simple approach can be readily...

Visible-light-induced decarboxylative and deboronative reactions using two-molecule organic photoredox catalysts, namely, phenanthrene (Phen) biphenyl (BP), as electron donors 9-cyano-10-methoxycarbonylanthracene 1a an acceptor were achieved. The high solubility of significantly improved the reaction efficiency product yield. In addition, facile tuning oxidation potential electron-donor molecule via replacement Phen with BP enabled application system to a wide range substrates.

Three different approaches to asymmetric induction in the cis-to-trans photoisomerization of a number 1-benzoyl-2,3-diphenylcyclopropane derivatives are reported: use chiral inductors and covalent auxiliaries MY zeolites ionic crystals. High levels were achieved using latter two methods-up 71% through remarkable 99% via solid state auxiliary approach. In zeolite method, diastereomeric excess was found depend strongly on nature cation, M(+), approach, evidence is presented that it fixed...

We developed a rhodium-catalyzed chain-walking hydrothiolation process for internal alkenes, which offers novel and efficient alternative C(sp3)–H bond cleavage, while focusing on thiol incorporation. This method exclusively affords N,S-acetals at 36–90% yields. Regioconvergent significantly improved the effectiveness of this transformation. Preliminary mechanistic investigations revealed that an amide-directing group is essential regioselective synthesis, underlining its significance in process.

Single electron transfer (SET)-photochemical decarboxylation of free carboxylic acids was performed in a polar solvent using several arenes such as phenanthrene, naphthalene, 1-methylnaphthalene, biphenyl, triphenylene, and chrysene the presence various acceptors 1,2-, 1,3-, 1,4-dicyanobenzenes, methyl 4-cyanobenzoate, 1,4-dicyanonaphthalene. The reaction influenced by arenes, acceptors, solvent. best result achieved photoreaction biphenyl 1,4-dicyanonaphthalene aqueous acetonitrile.

Photoinduced electron transfer (PET) promoted decarboxylation of α-(ω-carboxyalkyl) β-keto esters undergoes radical ring expansion and cyclization reactions. This mild environmentally friendly method can provide one-carbon expanded γ-keto bicyclic alcohols, the product distribution is strongly dependent on length alkyl chain containing terminal carboxylate group.

Proteinogenic amino acid residues that promote β-sheet secondary structure are hydrophobic (e.g., Ile or Val) only moderately polar Thr). The design of peptides intended to display in water typically requires one set ensure conformational stability and an orthogonal set, with charged side chains, aqueous solubility discourage self-association. Here we describe new acids manifest substantial propensity, by virtue β-branching, also bear ionizable group the chain.

Sequential radical addition to alkenes and reductive cyclization of phenylalanine tyrosine derivatives via photoinduced decarboxylation furnished ring-constrained γ-amino acids under mild conditions. A variety such as acrylamides acrylic esters could be employed in the cascade cyclization. The yields are dependent on electron-accepting ability steric hindrance alkene used. proposed sequential reaction can also applied for direct tethering dipeptides yield unique tetrapeptides.

Ergosterol peroxide (EPO, 1) is a major antitumor sterol produced by edible or medicinal mushrooms. Following oral administration of 1 to rats anaerobic in vitro incubation with rat fecal bacteria, three metabolites were detected and their structures identified be 5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (M1, 2), 5α,6α-epoxyergosta-8,22-diene-3β,7α-diol (M2, 3), 5α,6α-epoxy-3β-hydroxyergosta-22-ene-7-one (M3, 4) spectroscopic analysis. Of these, M2 M3 showed more potent inhibitory...

Metal-free photoinduced decarboxylative radical polymerization of aliphatic carboxylic acids with a variety monomers was found to proceed smoothly give the corresponding polymers under mild conditions. Complex such as those sugars, steroids, and peptides can function benign initiators via decarboxylation be incorporated at polymer chain ends. This synthetic methodology represents facile introduction molecules functionalities by using commercially available acids.

The side-chain functionalization of aspartic/glutamic acid derivatives through photoinduced decarboxylation was achieved by using organic two-molecule photoredox catalysts without racemization under mild conditions. A facile process involving the preparation substrates and decarboxylative radical additions can provide easy access to linked amino acids with carbohydrates at side chain.