Unknown

Dataset Information

0

Photocatalytic carbanion generation - benzylation of aliphatic aldehydes to secondary alcohols.

ABSTRACT: We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

SUBMITTER: Donabauer K 

PROVIDER: S-EPMC6524566 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Photocatalytic carbanion generation - benzylation of aliphatic aldehydes to secondary alcohols.

Donabauer Karsten K   Maity Mitasree M   Berger Anna Lucia AL   Huff Gregory S GS   Crespi Stefano S   König Burkhard B  

Chemical science 20190416 19

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO<sub>2</sub> extrusion and reduction of the <i>in situ</i> formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product. ...[more]

Similar Datasets

Unknown Spin-Center Shift-Enabled Direct Enantioselective ?-Benzylation of Aldehydes with Alcohols.
| S-EPMC5896313 | biostudies-other
Unknown Photocatalytic Barbier reaction - visible-light induced allylation and benzylation of aldehydes and ketones.
| S-EPMC6148494 | biostudies-literature
Unknown Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions.
| S-EPMC8133029 | biostudies-literature
Unknown Enantioselective ?-benzylation of aldehydes via photoredox organocatalysis.
| S-EPMC3056320 | biostudies-literature
Unknown Selective Oxidation of Biomass-Derived Alcohols and Aromatic and Aliphatic Alcohols to Aldehydes with O2/Air Using a RuO2-Supported Mn3O4 Catalyst.
| S-EPMC6644874 | biostudies-literature
Unknown Enantioselective homocrotylboration of aliphatic aldehydes.
| S-EPMC3560844 | biostudies-literature
Unknown Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols.
| S-EPMC6368192 | biostudies-literature
Unknown Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.
| S-EPMC6824429 | biostudies-literature
Unknown Conversion of Secondary C3-C4 Aliphatic Alcohols on Carbon Nanotubes Consolidated by Spark Plasma Sintering.
| S-EPMC7912505 | biostudies-literature
Unknown Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols.
| S-EPMC6273960 | biostudies-literature