---
_id: '12067'
abstract:
- lang: eng
  text: We present a divergent strategy for the fluorination of phenylacetic acid
    derivatives that is induced by a charge-transfer complex between Selectfluor and
    4-(dimethylamino)pyridine. A comprehensive investigation of the conditions revealed
    a critical role of the solvent on the reaction outcome. In the presence of water,
    decarboxylative fluorination through a single-electron oxidation is dominant.
    Non-aqueous conditions result in the clean formation of α-fluoro-α-arylcarboxylic
    acids.
article_processing_charge: No
article_type: original
author:
- first_name: Amiera
  full_name: Madani, Amiera
  last_name: Madani
- first_name: Lucia
  full_name: Anghileri, Lucia
  last_name: Anghileri
- first_name: Matthias
  full_name: Heydenreich, Matthias
  last_name: Heydenreich
- first_name: Heiko M.
  full_name: Möller, Heiko M.
  last_name: Möller
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
citation:
  ama: Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. Benzylic fluorination
    induced by a charge-transfer complex with a solvent-dependent selectivity switch.
    <i>Organic Letters</i>. 2022;24(29):5376–5380. doi:<a href="https://doi.org/10.1021/acs.orglett.2c02050">10.1021/acs.orglett.2c02050</a>
  apa: Madani, A., Anghileri, L., Heydenreich, M., Möller, H. M., &#38; Pieber, B.
    (2022). Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent
    selectivity switch. <i>Organic Letters</i>. American Chemical Society. <a href="https://doi.org/10.1021/acs.orglett.2c02050">https://doi.org/10.1021/acs.orglett.2c02050</a>
  chicago: Madani, Amiera, Lucia Anghileri, Matthias Heydenreich, Heiko M. Möller,
    and Bartholomäus Pieber. “Benzylic Fluorination Induced by a Charge-Transfer Complex
    with a Solvent-Dependent Selectivity Switch.” <i>Organic Letters</i>. American
    Chemical Society, 2022. <a href="https://doi.org/10.1021/acs.orglett.2c02050">https://doi.org/10.1021/acs.orglett.2c02050</a>.
  ieee: A. Madani, L. Anghileri, M. Heydenreich, H. M. Möller, and B. Pieber, “Benzylic
    fluorination induced by a charge-transfer complex with a solvent-dependent selectivity
    switch,” <i>Organic Letters</i>, vol. 24, no. 29. American Chemical Society, pp.
    5376–5380, 2022.
  ista: Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. 2022. Benzylic
    fluorination induced by a charge-transfer complex with a solvent-dependent selectivity
    switch. Organic Letters. 24(29), 5376–5380.
  mla: Madani, Amiera, et al. “Benzylic Fluorination Induced by a Charge-Transfer
    Complex with a Solvent-Dependent Selectivity Switch.” <i>Organic Letters</i>,
    vol. 24, no. 29, American Chemical Society, 2022, pp. 5376–5380, doi:<a href="https://doi.org/10.1021/acs.orglett.2c02050">10.1021/acs.orglett.2c02050</a>.
  short: A. Madani, L. Anghileri, M. Heydenreich, H.M. Möller, B. Pieber, Organic
    Letters 24 (2022) 5376–5380.
date_created: 2022-09-08T11:34:30Z
date_published: 2022-07-17T00:00:00Z
date_updated: 2023-05-08T08:39:34Z
day: '17'
doi: 10.1021/acs.orglett.2c02050
extern: '1'
intvolume: '        24'
issue: '29'
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: https://doi.org/10.26434/chemrxiv-2022-mstv5
month: '07'
oa: 1
oa_version: Published Version
page: 5376–5380
publication: Organic Letters
publication_identifier:
  eissn:
  - 1523-7052
  issn:
  - 1523-7060
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent
  selectivity switch
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 24
year: '2022'
...
---
_id: '11981'
abstract:
- lang: eng
  text: The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction
    suffers from poor functional group compatibility and limits their use as a protecting
    group. The visible-light-mediated debenzylation disclosed here renders benzyl
    ethers temporary protective groups, enabling new orthogonal protection strategies.
    Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic
    photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes,
    and alkynes. The reaction time can be reduced from hours to minutes in continuous
    flow.
article_processing_charge: No
article_type: letter_note
author:
- first_name: Cristian
  full_name: Cavedon, Cristian
  last_name: Cavedon
- first_name: Eric T.
  full_name: Sletten, Eric T.
  last_name: Sletten
- first_name: Amiera
  full_name: Madani, Amiera
  last_name: Madani
- first_name: Olaf
  full_name: Niemeyer, Olaf
  last_name: Niemeyer
- first_name: Peter H.
  full_name: Seeberger, Peter H.
  last_name: Seeberger
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
citation:
  ama: Cavedon C, Sletten ET, Madani A, Niemeyer O, Seeberger PH, Pieber B. Visible-light-mediated
    oxidative debenzylation enables the use of benzyl ethers as temporary protecting
    groups. <i>Organic Letters</i>. 2021;23(2):514-518. doi:<a href="https://doi.org/10.1021/acs.orglett.0c04026">10.1021/acs.orglett.0c04026</a>
  apa: Cavedon, C., Sletten, E. T., Madani, A., Niemeyer, O., Seeberger, P. H., &#38;
    Pieber, B. (2021). Visible-light-mediated oxidative debenzylation enables the
    use of benzyl ethers as temporary protecting groups. <i>Organic Letters</i>. American
    Chemical Society. <a href="https://doi.org/10.1021/acs.orglett.0c04026">https://doi.org/10.1021/acs.orglett.0c04026</a>
  chicago: Cavedon, Cristian, Eric T. Sletten, Amiera Madani, Olaf Niemeyer, Peter
    H. Seeberger, and Bartholomäus Pieber. “Visible-Light-Mediated Oxidative Debenzylation
    Enables the Use of Benzyl Ethers as Temporary Protecting Groups.” <i>Organic Letters</i>.
    American Chemical Society, 2021. <a href="https://doi.org/10.1021/acs.orglett.0c04026">https://doi.org/10.1021/acs.orglett.0c04026</a>.
  ieee: C. Cavedon, E. T. Sletten, A. Madani, O. Niemeyer, P. H. Seeberger, and B.
    Pieber, “Visible-light-mediated oxidative debenzylation enables the use of benzyl
    ethers as temporary protecting groups,” <i>Organic Letters</i>, vol. 23, no. 2.
    American Chemical Society, pp. 514–518, 2021.
  ista: Cavedon C, Sletten ET, Madani A, Niemeyer O, Seeberger PH, Pieber B. 2021.
    Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers
    as temporary protecting groups. Organic Letters. 23(2), 514–518.
  mla: Cavedon, Cristian, et al. “Visible-Light-Mediated Oxidative Debenzylation Enables
    the Use of Benzyl Ethers as Temporary Protecting Groups.” <i>Organic Letters</i>,
    vol. 23, no. 2, American Chemical Society, 2021, pp. 514–18, doi:<a href="https://doi.org/10.1021/acs.orglett.0c04026">10.1021/acs.orglett.0c04026</a>.
  short: C. Cavedon, E.T. Sletten, A. Madani, O. Niemeyer, P.H. Seeberger, B. Pieber,
    Organic Letters 23 (2021) 514–518.
date_created: 2022-08-25T11:13:05Z
date_published: 2021-01-15T00:00:00Z
date_updated: 2023-02-21T10:10:16Z
day: '15'
doi: 10.1021/acs.orglett.0c04026
extern: '1'
external_id:
  pmid:
  - '33400534'
intvolume: '        23'
issue: '2'
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: https://doi.org/10.1021/acs.orglett.0c04026
month: '01'
oa: 1
oa_version: Published Version
page: 514-518
pmid: 1
publication: Organic Letters
publication_identifier:
  eissn:
  - 1523-7052
  issn:
  - 1523-7060
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers
  as temporary protecting groups
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 23
year: '2021'
...
---
_id: '11982'
abstract:
- lang: eng
  text: A carbon nitride material can be combined with homogeneous nickel catalysts
    for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions.
    The metal-free heterogeneous semiconductor is fully recyclable and couples a broad
    range of electron-poor aryl bromides with primary and secondary alcohols as well
    as water. The application for intramolecular reactions and the synthesis of active
    pharmaceutical ingredients was demonstrated. The catalytic protocol is applicable
    for the coupling of aryl iodides with thiols as well.
article_processing_charge: No
article_type: letter_note
author:
- first_name: Cristian
  full_name: Cavedon, Cristian
  last_name: Cavedon
- first_name: Amiera
  full_name: Madani, Amiera
  last_name: Madani
- first_name: Peter H.
  full_name: Seeberger, Peter H.
  last_name: Seeberger
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
citation:
  ama: Cavedon C, Madani A, Seeberger PH, Pieber B. Semiheterogeneous dual nickel/photocatalytic
    (thio)etherification using carbon nitrides. <i>Organic Letters</i>. 2019;21(13):5331-5334.
    doi:<a href="https://doi.org/10.1021/acs.orglett.9b01957">10.1021/acs.orglett.9b01957</a>
  apa: Cavedon, C., Madani, A., Seeberger, P. H., &#38; Pieber, B. (2019). Semiheterogeneous
    dual nickel/photocatalytic (thio)etherification using carbon nitrides. <i>Organic
    Letters</i>. American Chemical Society. <a href="https://doi.org/10.1021/acs.orglett.9b01957">https://doi.org/10.1021/acs.orglett.9b01957</a>
  chicago: Cavedon, Cristian, Amiera Madani, Peter H. Seeberger, and Bartholomäus
    Pieber. “Semiheterogeneous Dual Nickel/Photocatalytic (Thio)Etherification Using
    Carbon Nitrides.” <i>Organic Letters</i>. American Chemical Society, 2019. <a
    href="https://doi.org/10.1021/acs.orglett.9b01957">https://doi.org/10.1021/acs.orglett.9b01957</a>.
  ieee: C. Cavedon, A. Madani, P. H. Seeberger, and B. Pieber, “Semiheterogeneous
    dual nickel/photocatalytic (thio)etherification using carbon nitrides,” <i>Organic
    Letters</i>, vol. 21, no. 13. American Chemical Society, pp. 5331–5334, 2019.
  ista: Cavedon C, Madani A, Seeberger PH, Pieber B. 2019. Semiheterogeneous dual
    nickel/photocatalytic (thio)etherification using carbon nitrides. Organic Letters.
    21(13), 5331–5334.
  mla: Cavedon, Cristian, et al. “Semiheterogeneous Dual Nickel/Photocatalytic (Thio)Etherification
    Using Carbon Nitrides.” <i>Organic Letters</i>, vol. 21, no. 13, American Chemical
    Society, 2019, pp. 5331–34, doi:<a href="https://doi.org/10.1021/acs.orglett.9b01957">10.1021/acs.orglett.9b01957</a>.
  short: C. Cavedon, A. Madani, P.H. Seeberger, B. Pieber, Organic Letters 21 (2019)
    5331–5334.
date_created: 2022-08-25T11:18:00Z
date_published: 2019-07-05T00:00:00Z
date_updated: 2023-02-21T10:10:19Z
day: '05'
doi: 10.1021/acs.orglett.9b01957
extern: '1'
external_id:
  pmid:
  - '31247752'
intvolume: '        21'
issue: '13'
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: https://doi.org/10.1021/acs.orglett.9b01957
month: '07'
oa: 1
oa_version: Published Version
page: 5331-5334
pmid: 1
publication: Organic Letters
publication_identifier:
  eissn:
  - 1523-7052
  issn:
  - 1523-7060
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Semiheterogeneous dual nickel/photocatalytic (thio)etherification using carbon
  nitrides
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 21
year: '2019'
...
---
_id: '11983'
abstract:
- lang: eng
  text: A continuous process for the synthesis and inline separation of anhydrous
    trifluoromethyl diazomethane in a single continuous flow process is presented.
    The diazo building block is generated from the corresponding amine and NaNO2 under
    acidic, aqueous conditions and subsequently diffuses through a gas-permeable membrane
    into an organic stream. To avoid storage and transportation of the hazardous compound,
    a representative downstream process in a packed-bed reactor yielding highly functionalized
    building blocks was developed.
article_processing_charge: No
article_type: letter_note
author:
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
- first_name: C. Oliver
  full_name: Kappe, C. Oliver
  last_name: Kappe
citation:
  ama: Pieber B, Kappe CO. Generation and synthetic application of trifluoromethyl
    diazomethane utilizing continuous flow technologies. <i>Organic Letters</i>. 2016;18(5):1076-1079.
    doi:<a href="https://doi.org/10.1021/acs.orglett.6b00194">10.1021/acs.orglett.6b00194</a>
  apa: Pieber, B., &#38; Kappe, C. O. (2016). Generation and synthetic application
    of trifluoromethyl diazomethane utilizing continuous flow technologies. <i>Organic
    Letters</i>. American Chemical Society. <a href="https://doi.org/10.1021/acs.orglett.6b00194">https://doi.org/10.1021/acs.orglett.6b00194</a>
  chicago: Pieber, Bartholomäus, and C. Oliver Kappe. “Generation and Synthetic Application
    of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies.” <i>Organic
    Letters</i>. American Chemical Society, 2016. <a href="https://doi.org/10.1021/acs.orglett.6b00194">https://doi.org/10.1021/acs.orglett.6b00194</a>.
  ieee: B. Pieber and C. O. Kappe, “Generation and synthetic application of trifluoromethyl
    diazomethane utilizing continuous flow technologies,” <i>Organic Letters</i>,
    vol. 18, no. 5. American Chemical Society, pp. 1076–1079, 2016.
  ista: Pieber B, Kappe CO. 2016. Generation and synthetic application of trifluoromethyl
    diazomethane utilizing continuous flow technologies. Organic Letters. 18(5), 1076–1079.
  mla: Pieber, Bartholomäus, and C. Oliver Kappe. “Generation and Synthetic Application
    of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies.” <i>Organic
    Letters</i>, vol. 18, no. 5, American Chemical Society, 2016, pp. 1076–79, doi:<a
    href="https://doi.org/10.1021/acs.orglett.6b00194">10.1021/acs.orglett.6b00194</a>.
  short: B. Pieber, C.O. Kappe, Organic Letters 18 (2016) 1076–1079.
date_created: 2022-08-25T11:22:20Z
date_published: 2016-03-04T00:00:00Z
date_updated: 2023-02-21T10:10:21Z
day: '04'
doi: 10.1021/acs.orglett.6b00194
extern: '1'
external_id:
  pmid:
  - '26902154'
intvolume: '        18'
issue: '5'
language:
- iso: eng
month: '03'
oa_version: None
page: 1076-1079
pmid: 1
publication: Organic Letters
publication_identifier:
  eissn:
  - 1523-7052
  issn:
  - 1523-7060
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Generation and synthetic application of trifluoromethyl diazomethane utilizing
  continuous flow technologies
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 18
year: '2016'
...