Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

Karsten Donabauer; Mitasree Maity; Anna Lucia Berger; Gregory S. Huff; Stefano Crespi; Burkhard König

doi:10.1039/c9sc01356c

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

Karsten Donabauer
, Mitasree Maity
, Anna Lucia Berger
, Gregory S. Huff
, Stefano Crespi
, Burkhard König^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

95 Citations (Scopus)

79 Downloads (Pure)

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.

Original language	English
Pages (from-to)	5162-5166
Number of pages	5
Journal	Chemical Science
Volume	10
Issue number	19
DOIs	https://doi.org/10.1039/c9sc01356c
Publication status	Published - 2019
Externally published	Yes

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Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcoholsFinal publisher's version, 1.05 MBLicence: CC BY-NC

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@article{006ce6b8f0ce43f7879836c09d28fd1a,

title = "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.",

author = "Karsten Donabauer and Mitasree Maity and Berger, \{Anna Lucia\} and Huff, \{Gregory S.\} and Stefano Crespi and Burkhard K{\"o}nig",

note = "Funding Information: This work was supported by the German Science Foundation (DFG, KO 1537/18-1). This project has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 Research and Innovation Programme (grant agreement No. 741623). We thank Dr Rudolf Vasold for GC-MS measurements, Nele Berg for in situ NMR-measurements, the X-Ray department for crystal structure analysis and Regina Hoheisel for CV measurements. Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c9sc01356c",

language = "English",

volume = "10",

pages = "5162--5166",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "ROYAL SOC CHEMISTRY",

number = "19",

}

TY - JOUR

T1 - Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

AU - Donabauer, Karsten

AU - Maity, Mitasree

AU - Berger, Anna Lucia

AU - Huff, Gregory S.

AU - Crespi, Stefano

AU - König, Burkhard

N1 - Funding Information: This work was supported by the German Science Foundation (DFG, KO 1537/18-1). This project has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 Research and Innovation Programme (grant agreement No. 741623). We thank Dr Rudolf Vasold for GC-MS measurements, Nele Berg for in situ NMR-measurements, the X-Ray department for crystal structure analysis and Regina Hoheisel for CV measurements. Publisher Copyright: © 2019 The Royal Society of Chemistry.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85066249912

U2 - 10.1039/c9sc01356c

DO - 10.1039/c9sc01356c

M3 - Article

AN - SCOPUS:85066249912

SN - 2041-6520

VL - 10

SP - 5162

EP - 5166

JO - Chemical Science

JF - Chemical Science

IS - 19

ER -

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

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