Aerobic oxidation of C-H bonds to carboxylic acids enabled by decatungstate photocatalysis

Photoinduced Radical Sulfinylation of C(sp3)–H Bonds with Sulfinyl Sulfones

“…In recent years, photocatalytic hydrogen atom transfer (HAT) has emerged as a versatile strategy for late-stage C­(sp 3 )–H functionalization. , This activation mode can conveniently transfer strong C­(sp 3 )–H bonds to carbon-centered radicals without the limitation of redox potentials of substrates. These radicals can be subjected to numerous transformations, including the formation of C–C, ,, C–N, , C–O, C–F, and C–S bonds.…”

“…We commenced the investigations using the photo-HAT catalyst decatungstate anion ([W 10 O 32 ] 4– ), which has been widely explored due to its strong ability to cleave inert C–H bonds . First, the reaction of cyclohexane 1a with sodium p -toluenesulfinate 2a was carried out in the presence of tetrakis­(tetrabutylammonium) decatungstate (TBADT, 4 mol %) and acetyl chloride in CH 3 CN/H 2 O (9:1) upon irradiation with a Kessil 40 W 370 nm lamp for 12 h (Table , entry 1).…”

Synthesis of C-1 Deuterated 3-Formylindoles by Organophotoredox Catalyzed Direct Formylation of Indoles with Deuterated Glyoxylic Acid

“…Although significant efforts have been made to synthesize C1-deuterated aryl aldehydes, − no study has focused on the preparation of the deuterated 3-formylindoles. Xie and co-workers reported an elegant photoredox mediated deoxygenative deuteration of carboxylic acids with D 2 O, but only one example of a deuterated 2-formyl N -methylindole was described in their study .…”

“…Our group, the group of Bertrand and Yan, and other groups have independently developed an NHC promoted H/D exchange reaction at the formyl group with D 2 O . Moreover, our group and those of Wang and Wu reported photoredox mediated formyl H/D exchange reactions using D 2 O as deuterium source . All these methods use prefunctionalized aldehydes as reactants.…”

Transformation of triolein to biogasoline by photo-chemo-biocatalysis

“…[37][38][39][40] These drawbacks motivate the development of alternative methods of oxidative cleavage. Molecular oxygen (O 2 ) is considered a clean, cheap oxidant, [41][42][43][44][45] and may be ideal for the oxidative cleavage of oleic acid.…”