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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

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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]

PMID: 31183069

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